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| Chlorovulones, new halogenated marine prostanoids with an antitumor activity from the stolonifer clavularia viridis Quoy and Gaimard Tetrahedron Letters, Volume 26, Issue 47, 1985, Pages 5787-5790 Kazuo Iguchi, Soichiro Kaneta, Kenichiro Mori, Yasuji Yamada, Atsushi Honda, Yo Mori | ||||
| Absolute stereochemistry of new prostanoids clavulone I, II and III, from Tetrahedron Letters, Volume 24, Issue 14, 1983, Pages 1549-1552 Hiroyuki Kikuchi, Yasumasa Tsukitani, Kazuo Iguchi and, Yasuji Yamada | ||||
| Enantioselective synthesis of (−)-gephyrotoxine 223AB [(3R,5R,9R)-3-butyl-5-propyloctahydroindolizine] Tetrahedron: Asymmetry, Volume 4, Issue 7, July 1993, Pages 1429-1430 Anne Fleurant, Jean Pierre Célérier, Gérard Lhommet | ||||
C10H21NO E.e.>98%, [α]22D =−20.2 (c=0.56, CHCl3 Source of chirality: (S)-pyroglutamic acid (U.C.I.B. France) Absolute configuration: 2(S), 5(R)
(2S,5R)-1-carbobenzyloxy-2-hydroxyethyl-5-butylpyrrolidine
C18H27NO3 E.e.>98%, [α]20D =−31.7 (c=1.25, CHCl3) Source of chirality: (S)-pyroglutamic acid (U.C.I.B. France) Absolute configuration: 2(S), 5(R)
(2S,5R)-l-carbobenzyloxy-2-(l-oxoethyl)-5-butylpyrrolidine
C18H25NO3 E.e.>98%, [α]20D =−44.7 (c=1.05, CHCL3) Source of chirality: (S)-pyroglutamic acid (U.C.I.B. France) Absolute configuration: 2(S), 5(R)
(2R,5R)-1-carbobenzyloxy-2-(4-oxoheptyl)-5-butylpyrrolidine
C23H35NO3 E.e.>98%, [α]20D =−52.5 (c=0.63, CH2Cl2) Source of chirality: (S)-pyroglutamic acid (U.C.I.B. France) Absolute configuration: 2(R), 5(R) (Assigned by correlation of specific rotation with literature)
(3R,5R,9R)-3-Butyl-5-propyloctahydroindolizine
C15H29N (−) - Gephyrotoxine 223AB E.e.>98%, [α]20D=−103 (c=1.12, Hexane) Source of chirality: (S)-pyroglutamic acid (U.C.I.B. France) Absolute configuration: 3(R), 5(R), 9(R) (Assigned by correlation of specific rotation with literature)
| Reversal of expected stereochemical outcome in the oppolzer reaction of a cyclic N-enoylsultam: Enantioselective synthesis and absolute configuration of antispermatogenic hexahydroindeno[1,2-c]pyridines Tetrahedron Letters, Volume 38, Issue 21, 26 May 1997, Pages 3691-3694 Joseph M. Jump, Andrew T. McPhail, C. Edgar Cook | ||||
| The first enantioselective synthesis of poly-oxygenated α-hydroxydihydrochalcones and circular dichroic assessment of their absolute configuration Tetrahedron Letters, Volume 28, Issue 41, 1987, Pages 4857-4860 Barend C. B. Bezuidenhoudt, Annelie Swanepoel, Jan A.N. Augustyn, Daneel Ferreira | ||||
| Enantioselective synthesis of tacrine-hyperzine A hybrids. Preparative chiral MPLC separation of their racemic mixtures and absolute configuration assignments by X-ray diffraction analysis Tetrahedron: Asymmetry, Volume 9, Issue 5, 13 March 1998, Pages 835-849 Pelayo Camps, Joan Contreras, Mercè Font-Bardia, Jordi Morral, Diego Muñoz-Torrero, Xavier Solans | ||||
| Enantioselective synthesis and absolute configuration of myoporone Tetrahedron, Volume 49, Issue 29, 1993, Pages 6515-6520 Ramesh C. Anand, Vibha Singh | ||||
| First enantioselective synthesis and determination of the absolute configuration of natural (+)-dehydro-β-monocyclonerolidol Tetrahedron Letters, Volume 44, Issue 34, 18 August 2003, Pages 6463-6464 Elie Palombo, Gérard Audran, Honoré Monti | ||||
| The first enantioselective synthesis of (S)-5-bromo-3-(1-methyl-2-pyrrolidinyl)pyridine: a key intermediate for the preparation of SIB-1508Y Tetrahedron: Asymmetry, Volume 12, Issue 8, 21 May 2001, Pages 1121-1124 François-Xavier Felpin, Giang Vo-Thanh, Jean Villiéras, Jacques Lebreton | ||||
C9H10BrNO E.e.=94% [α]D20=16.2 (c 1.47, MeOH) Source of chirality: asymmetric synthesis Absolute configuration: (R)
Methanesulfonic acid 1-(5-bromopyridin-3-yl)but-3-enyl ester
C10H13NO3S [α]D20=−50 (c 1.2, MeOH) Source of chirality: asymmetric synthesis Absolute configuration: (R)
3-(1-Azido-but-3-enyl)-5-bromopyridine
C9H9BrN4 [α]D20=−81.8 (c 1.29, MeOH) Source of chirality: asymmetric synthesis Absolute configuration: (S)
| Novel C-20-oxygenated prostanoids, 20-acetoxyclavulones, from the stolonifer Tetrahedron Letters, Volume 24, Issue 41, 1983, Pages 4433-4434 Kazuo Iguchi, Yasuji Yamada, Hiroyuki Kikuchi and, Yasumasa Tsukitani | ||||
| Convolutamydine A: the first authenticated absolute configuration and enantioselective synthesis Tetrahedron: Asymmetry, Volume 17, Issue 22, 27 November 2006, Pages 3070-3074 Giancarlo Cravotto, Giovanni B. Giovenzana, Giovanni Palmisano, Andrea Penoni, Tullio Pilati, Massimo Sisti, Federica Stazi | ||||
C11H9Br2NO3 Source of chirality: (−)-(1R,2S,5R)-8-phenylmenthol Absolute configuration: (3R) (c 0.20, MeOH)
| Enantioselective synthesis of substituted octalones Tetrahedron: Asymmetry, Volume 5, Issue 8, August 1994, Pages 1433-1434 Lúcia C. Sequeira, Paulo R. R. Costa, Alexandre Neves, Pierre Esteves | ||||
C13H20O4 [α]D =+4.6 (c = 2.8; CCl4) (88% ee - by 1H NMR using [Eu(hfc)3]) Source of chirality: (S)-(−)-l-phenylethylamine Absolute configuration: S
(R)-(−)-2-carbethoxy-2-(3-oxobutyl)-1,4-cyclohexanedionemonoethylamine ketal
C15H22O6 [α]D = −36 (c = 3; CCl4) (76% ee, by [Eu(hfc)3]) Source of chirality: (S)-(−)-1-phenyletylamine Absolute configuration: R
(R)-(−)-6,6-(ethylenedioxy)-10-carbethoxy-Δ 1 (9)-octal-2-one
C15H20O5 [α]D = −108 (c=0.5;CCl4) Source of chirality: (S)-(−)-phenylethylamine Absolute configuration: R
(S)-(−)-6,6-(ethylenedioxy)-10-methyl-Δ1 (9) - octal-2-one
C13H18O3 [α]D = - 171 (c= 0.9; CCl4) Source of chirality: (S)-(−)-1-phenylethylamine Absolute configuration: S
| Absolute configuration of (−)-solanapyrone A Tetrahedron Letters, Volume 26, Issue 20, 1985, Pages 2453-2454 Akitami Ichihara, Masayoshi Miki, Sadao Sakamura | ||||
| Enzyme catalysed lactonization of 3,5 dihydroxy esters: Enantioselective synthesis of naturally occurring 3-hydroxy-5-decanolide, (−)-massoialactone, and 3-hydroxy-5-icosanolide. Tetrahedron: Asymmetry, Volume 3, Issue 1, 1992, Pages 29-32 Carlo Bonini, Piero Pucci, Rocco Racioppi, Licia Viggiani | ||||
C10H18O3 Absolute configuration 4R, 6R. Source of chirality: natural and biocatalytic lactonization E.e. = 86% on synthetic on (determined by1H-NMR on (−) camphanic acid derivative). [α]D=+ 26 (c= 1.2, CHCl3)
2-Decen-5-olide (Massoialactone)
C10H16O2 Absolute configuration 6R Source of chirality: natural and synthetic by dehydration of 3-Hydroxy-5-decanolide E.e. = 86% on synthetic one [α]D= − 84 (c= 1.8, CHCl3)
3-Hydroxy-5-icosanolide
C20H38O3 Absolute configuration 3R, 5R Source of chirality: biocatalityc lactonization E.e. = 98% (determined by1H-NMR on (−) camphanic acid derivative). [α]D= +84 (c=1, CHCl3).
2-Icosen-5-olide
C20H36O2 Absolute configuration 5R Source of chirality: synthetic by dehydration of 3-Hydroxy-5-icosanolide [α]D= −42 (c=0.5, CHCl3).
| Enantioselective synthesis of 1-metallocenylalkanols by catalytic asymmetric alkylation of metallocenecarboxaldehydes with dialkylzincs Tetrahedron: Asymmetry, Volume 4, Issue 8, August 1993, Pages 1763-1766 Yonetatsu Matsumoto, Akira Ohno, Shi-jie Lu, Tamio Hayashi, Nobuki Oguni and, Masahiko Hayashi | ||||
C13H16OFe E.e. = >96% [by 1H NMR in the presence of Eu(hfc)3] [α]D20 −57.5 (c 1.0, benzene) Source of chirality: Enantioselective ethylation with diethylzinc Absolute configuration: R (assigned by mechanistic considerations)
1-Ferrocenylethanol
C12H14OFe E.e. = >99% [by optical rotation] [α]D25 −31.1 (c 1.0, benzene) Source of chirality: Enantioselective methylation with dimethylzinc Absolute configuration: R (assigned by optical rotation)
1 -Ruthenocenylpropanol
C13H16ORu E.e. = >96% [by 1H NMR in the presence of Eu(hfc)3] [α]D20 −49.0 (c 1.1, benzene) Source of chirality: Enantioselective ethylation with diethylzinc Absolute configuration: R (assigned by mechanistic considerations)
1-Ruthenocenylethanol
C12H14ORu E.e. = 90% [by HPLC on Sumichiral OA-1100] [α]D20 −24.0 (c 0.5, benzene) Source of chirality: Enantioselective methylation with dimethylzinc Absolute configuration: R (assigned by mechanistic considerations)
N,N-Dimethyl-1-ferrocenylpropylamine
C15H21NFe E.e. = >96% [% e.e. of the precursor] [α]D20 −43.8 (c 1.0, benzene) Source of chirality: (R)-1-Ferrocenypropanol Absolute configuration: R (assigned by correlation with (R)-1-ferrocenypropanol)
N, N-Dimethyl-1-ferrocenylethylamine
C14H19NFe E.e. = >99% [by optical rotation] [α]D25 −14.2 (c 1.0, ethanol) Source of chirality: (R)-1-Ferrocenyethanol Absolute configuration: R (assigned by optical rotation)
N,N-Dimethyl-1-ruthenocenylpropylamine
C15H21NRu E.e. = >96% [% e.e. of the precursor] [α]D20 +13.2 (c 1.0, benzene) Source of chirality: (R)-1-Ruthenocenylpropanol Absolute configuration: R (assigned by correlation with (R)-1-ruthenocenylpropanol)
N,N-Dimethyl-1-ruthenocenylethylamine
C14H19NRu E.e. = 90% [% e.e. of the precursor] [α]D22 +22.1 (c 1.8, benzene) Source of chirality: (R)-1-Ruthenocenylethanol Absolute configuration: R (assigned by correlation with (R)-1-ruthenocenylethanol)
| An efficient synthetic route to chiral 4-alkyl-1,2,3,4-tetrahydroquinolines: enantioselective synthesis of (R)-4-ethyl-1,2,3,4-tetrahydroquinoline Tetrahedron: Asymmetry, Volume 11, Issue 23, 1 December 2000, Pages 4687-4691 Neelakandha S. Mani, Min Wu | ||||
C11H14O2 Ee=86% [α]D25= −17.3 (c=0.55, EtOH) Source of chirality: asymmetric synthesis Absolute configuration: R
(R)-3-Ethyl-1-indanone
C11H12O Ee=86% [α]D25= −15.5 (c=0.67, EtOH) Source of chirality: asymmetric synthesis Absolute configuration: R
(R)-3-Ethyl-1-indanone oxime
C11H13NO Ee=86% [α]D25= +18.6 (c=0.6, EtOH) Source of chirality: asymmetric synthesis Absolute configuration: R
(R)-4-Ethyl-1,2,3,4-tetrahydroquinoline
C11H15N Ee=86% [α]D25= +29.1 (c=1.4, EtOH) Source of chirality: asymmetric synthesis Absolute configuration: R
| Enantioselective synthesis of (R)-(+)-β-piperonyl-γ-butyrolactone Tetrahedron: Asymmetry, Volume 5, Issue 7, July 1994, Pages 1219-1220 Hiram C.A. Filho, Ubiracir F.L. Filho, Sergio Pinheiro, Mario L.A.A. Vasconcellos, Paulo R.R. Costa | ||||
Compound formula [α]25D = −26 (c = 1, CHCl3). e.e = 100% Source of chirality: (−)-10-dicyclohexylsulfamoyl-D-isoborneol Absolute configuration: 1S, 2R.
2-allyl-3-[(3′,4′-methylenedioxy)phenyl]propanoic acid, (1R, 2S)-10-(N,N,dicyclohexylaminesulfamoyl)born-2-yl ester.
Compound formula [α]25D = +22 (c = 1.8, CHCl3). d.e = 94% (det. by 1H NMR) Source of chirality: (+)-10-dicyclohexylsulfamoyl-L-isoborneol Absolute configuration of α-carbonyl stereocenter: S
(2S)-(−)-2-allyl-[3′,4′-(methylenedioxy)phenyl] propan-1-ol.
Compound formula [α]25D = −10 (c = 0.5, CHCl3). Source of chirality: (+)-10-dicyclohexylsulfamoyl-L-isoborneol Absolute configuration: S
(R)-(+)-β-piperonyl-γ-butyrolactone
Compound formula [α]25D = +3.1 (c = 3.8, CHCl3). Source of chirality: (+)-10-dicyclohexylsulfamoyl-L-isoborneol Absolute configuration: R
(2S)-(+)-2-alyl-[3′,4′-(methylenedioxy)phenyl] propan-1-ol, acetate.
Compound formula [α]25D = 11,8 (c = 1.3, CHCl3). e.e = 86% (det. by 1H NMR using Eu(hfc)3) Source of chirality: (+)-10-dicyclohexylsulfamoyl-L-isoborneol Absolute configuration: S
4-pentenoic acid, (1R, 2S)-10-(N,N,dicyclohexylaminesulfamoyl)born-2-yl ester.
Compound formula [α]25D = +4.0 (c = 3.6, CHCl3). e.e = 100% Source of chirality: (+)-10-dicyclohexylsulfamoyl-L-isoborneol Absolute configuration: 1R, 2S
| Directed metalation/ligand coupling approach to the enantioselective synthesis of 1,1′-binaphthyls Tetrahedron: Asymmetry, Volume 4, Issue 12, 1993, Pages 2423-2426 Robert W. Baker, Geoffrey R. Pocock, Melvyn V. Sargent, Edi Twiss (née Stanojevic) | ||||
C14H16OS E.e = >99.5% (by HPLC on DNB-[D]-PHGLY Pirkle column) [α]D −94 (c 1.05, toluene) Source of chirality: (1R)-menthyl (S)-p-toluenesulfinate Absolute configuration: S
(R)-1-t-Butylsulfinylnaphthalene
C14H16OS E.e. = >99% (by HPLC on DNB-[D]-PHGLY Pirkle column) [α]D +333 (c 1.10, toluene) Source of chirality: (1R)-menthyl (S)-1-naphthalenesulfinate Absolute configuration: R
Isopropyl (R)-1-t-butylsulfinyl-2-naphthalenecarboxylate
C18H22O3S E.e = 99.5% (by HPLC on DNB-[D]-PHGLY Pirkle column) [α]D +129 (c 1.30, toluene) Source of chirality: (1R)-menthyl (S)-1-naphthalenesulfinate Absolute configuration: R
(R)-N,N-Dimethyl-1-t-butylsulfinyl-2-naphthalenecarboxamide
C17H21NO2S E.e = ≥95% (inferred from subsequent transformation) [α]D +109 (c 0.375, toluene) Source of chirality: (1R)-menthyl (S)-1-naphthalenesulfinate Absolute configuration: R
Isopropyl (R)-1,1′-binaphthyl-2-carboxylate
C24H20O2 E.e. = 95% (by 300MHz 1H NMR with Eu(hfc)3) [α]D +12.8 (c 1.72, toluene) Source of chirality: (1R)-menthyl (S)-1-naphthalenesulfinate Absolute configuration: R
(R)-N,N-Dimethyl-1,1′-binaphthyl-2-carboxamide
C23H19NO E.e. = 94.8% (by HPLC on DNB-[D]-PHGLY Pirkle column) [α]D +86 (c 0.925, toluene) Source of chirality: (1R)-menthyl (S)-1-naphthalenesulfinate Absolute configuration: R
| A chiral synthesis of (8R,8aS)-hexahydro-8-methyl-5(1H)-indolizinone Tetrahedron: Asymmetry, Volume 4, Issue 7, July 1993, Pages 1405-1408 Akiharu Satake, Isao Shimizu | ||||
C18H26O4 E.e =>98 % by 1H NMR in the presence of Eu(TFC)3 [α]24D+29.0 (C4.4, CHCl3) Source of chirality: Sharpless asymmetric epoxidation Absolute configuration 4R, 5R
(8R,8aS)-hexahydro-8-methyl-5(1H)-indolizinone
C9H15ON D.e =>99%by 1H NMR [α]24D−21.5(0 0.65, CHCl3) Source of chirality: Sharpless asymmetric epoxidation Absolute configuration 8R, 8aS
(S)-6-(p-toluenesulfinyl)hex-5-yn-2-on3 ethytene acetal E.e.=100% [α]D23=+65.8 (c 0.152, CHCl3) Source of Chirality: H-menthol and well-established Anderson method Absolute configuration: S (based on the mechanism of the Andersen method)
Z-(R)-5-methyl-6-(p-toluenesulfinyl)hex-5-en-2-one ethylene acetal E.e.=100% [α]D23 −227.2 (c 0.340, CHCl3) Source of chirality: (−)-menthol Absolute configuration: R
| A method for the catalytic enantioselective synthesis of 6-silylated 2-cyclohexenones Tetrahedron Letters, Volume 47, Issue 14, 3 April 2006, Pages 2319-2321 Min Ge, E.J. Corey | ||||
| Metal halide-mediated opening of three membered rings: enantioselective synthesis of 2S,3R)-3-amino-2hydroxydecanoic acid and (3r)-3-aminodecanoic acid Tetrahedron: Asymmetry, Volume 8, Issue 21, 13 November 1997, Page 3513 | ||||
| The first enantioselective synthesis of α-aminophosphinates Tetrahedron Letters, Volume 44, Issue 24, 9 June 2003, Pages 4603-4606 Andrea Szabó, Zsuzsa M Jászay, László Hegedűs, László Tőke, Imre Petneházy | ||||
| Assignment of absolute configuration of 2-substituted-1-propanols by 1H NMR spectroscopy Tetrahedron Letters, Volume 27, Issue 34, 1986, Pages 4033-4034 Fujiko Yasuhara, Shozo Yamaguchi, Ryoji Kasai, Osamu Tanaka | ||||
| Absolute configuration of crotsparine, crotsparinine and sparsiflorine Tetrahedron, Volume 28, Issue 17, 1972, Pages 4579-4582 D. S. Bhakuni, S. Satish, M. M. Dhar | ||||
| 1,3-Asymmetric induction: Highly enantioselective synthesis of α-amino acids via 2,5-trans disubstituted imidazolidin-4-ones Tetrahedron Letters, Volume 32, Issue 17, 22 April 1991, Pages 1971-1974 Rosa Amoroso, Giuliana Cardillo, Claudia Tomasini | ||||
| Aldol reaction of 4-trimethylsiloxy-6-methylene-1,3-dioxines with chiral aldehydes: Enantioselective synthesis of 1,3-dioxin-4-ones having a 2,3-dihydroxylated alkyl group at the 6-position Tetrahedron: Asymmetry, Volume 3, Issue 9, September 1992, Pages 1157-1160 Masayuki Sato, Yoshiaki Sugita, Yumi Abiko, Chikara Kaneko | ||||
| On the stereoselectivity of the α-alkylation of β-hydroxy esters. Enantioselective synthesis of 4,4- and 6,6-disubstituted cyclohex-2-en-1-ones. Tetrahedron Letters, Volume 22, Issue 5, 1981, Pages 425-428 György Fráter | ||||
| Enantioselective synthesis of α-functionally-substituted cyclohexanones Tetrahedron Letters, Volume 21, Issue 47, 1980, Pages 4511-4514 Bernard de Jeso, Jean-Claude Pommier | ||||
| A short enantioselective synthesis of 1-deoxy- Tetrahedron Letters, Volume 40, Issue 8, 19 February 1999, Pages 1437-1440 Doron Shabat, Benjamin List, Richard A. Lerner, Carlos F. Barbas III | ||||
| A facile enantioselective synthesis of 2-(2-aminoethyl)allylsilanes, new synthons for piperidine synthesis Tetrahedron Letters, Volume 44, Issue 31, 28 July 2003, Pages 5785-5787 Jérémy Monfray, Yvonne Gelas-Mialhe, Jean-Claude Gramain, Roland Remuson | ||||
| Enantioselective synthesis of (2S)-1-benzyloxy-2,3-propanediol and (2R)-1-amino-2,3-propamediol from glycerol Tetrahedron: Asymmetry, Volume 1, Issue 4, 1990, Pages 219-220 Ching-Yun Hsu, Yi-Sho Lin, Biing-Jiun Uang | ||||
| First total synthesis of niphatesines A-D and assignment of absolute configuration Tetrahedron Letters, Volume 34, Issue 51, 17 December 1993, Pages 8329-8332 AV Rama Rao, Gongiti Ravindra Reddy | ||||
| Enzymatic resolution of 3-bromo-cyclohept-2-enol: application to the determination of the absolute configuration of diethyl (3-hydroxy-cyclohept-1-enyl)phosphonate Tetrahedron: Asymmetry, Volume 14, Issue 24, 12 December 2003, Pages 3857-3860 Mireille Attolini, Gilles Iacazio, Gilbert Peiffer, Michel Maffei | ||||
C7H11BrOE.e. >99% (by GC)[α]D20=−10.6 (c 0.59, CH2Cl2)Source of chirality: enzymatic resolutionAbsolute configuration: (S)
(R)-(+)-3-Acetoxy-1-bromo-cyclohept-1-ene
C9H13BrO2E.e.=91% (by GC)[α]D20=+39.5 (c 0.16, CH2Cl2)Source of chirality: enzymatic resolutionAbsolute configuration: (R)
(S)-(+)-Diethyl (3-hydroxy-cyclohept-1-enyl)phosphonate
C11H21O4PE.e. >99% (by GC)[α]D20=+9.9 (c 0.49, CH2Cl2)Source of chirality: asymmetric syntheisAbsolute configuration: (S)
| Enantiomer separation and absolute configuration of densely functionalized 2-oxatricyclo[4.3.1.03,8]decanes by CD spectroscopy and chemical correlation Tetrahedron: Asymmetry, Volume 11, Issue 15, 11 August 2000, Pages 3053-3057 Eugenius Butkus, Ulf Berg, Albinas | ||||
| Enantioselective synthesis of 1-alkyl-substituted 1-phenyl-1,2-ethanediols using a myrtenal-derived chiral auxiliary Tetrahedron: Asymmetry, Volume 14, Issue 20, 17 October 2003, Pages 3225-3232 María Elena Vargas-Díaz, Luis Chacón-García, Pedro Velázquez, Joaquín Tamariz, Pedro Joseph-Nathan, L. Gerardo Zepeda | ||||
C18H22O2SDr >99% (NMR)[α]25D=−68.4Source of chirality: (−)-myrtenalAbsolute configuration: (1S,2R,5R,7S,9R)
(1S,2R,5R,7S,9R)-5-[(1′S)-1′-Hydroxy-1′-phenyl-1′-ethyl)]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.02,7]undecane
C19H26O2SDr >99% (NMR)[α]25D=−62.4Source of chirality: (−)-myrtenalAbsolute configuration: (1S,2R,5R,7S,9R,1′S)
(1S,2R,5R,7S,9R)-5-[(1′S)-1′-Hydroxy-1′-phenyl-1′-propyl)]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.02,7]undecane
C20H28O2SDr >99% (NMR)[α]25D=−72.8Source of chirality: (−)-myrtenalAbsolute configuration: (1S,2R,5R,7S,9R,1′S)
(1S,2R,5R,7S,9R)-5-[(1′S)-1′-Hydroxy-2′-methyl-1′-phenyl-1′-propyl)]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.02,7]undecane
C21H30O2SDr >99% (NMR)[α]25D=−68.1Source of chirality: (−)-myrtenalAbsolute configuration: (1S,2R,5R,7S,9R,1′S)
(1S,2R,5R,7S,9R)-5-[(1′S)-1′-Hydroxy-1′,2′-diphenyl-1′-ethyl)]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.02,7]undecane
C25H30O2SDr >99% (NMR)[α]24D=−86.6Source of chirality: (−)-myrtenalAbsolute configuration: (1S,2R,5R,7S,9R,1′S)
(1S,2R,5R,7S,9R)-5-[(1′S)-1′-Hydroxy-3′-methyl-1′-phenyl-1′-butyl)]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.02,7]undecane
C22H32O2SDr >99% (NMR)[α]20D=−68.8Source of chirality: (−)-myrtenalAbsolute configuration: (1S,2R,5R,7S,9R,1′S)
(1S,2R,5R,7S,9R)-5-[(1′S)-1′-Hydroxy-1′-phenyl-2′-propen-1′-yl)]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.02,7]undecane
C20H26O2SDr >99% (NMR)[α]25D=−68.1Source of chirality: (−)-myrtenalAbsolute configuration: (1S,2R,5R,7S,9R,1′S)
(1S,2R,5R,7S,9R)-5-[(1′S)-1′-Hydroxy-1′,3′-diphenyl-2′-propyn-1′-yl)]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.02,7]undecane
C26H28O2SDr >99% (NMR)[α]25D=−27.1Source of chirality: (−)-myrtenalAbsolute configuration: (1S,2R,5R,7S,9R,1′S)
(1S,2R,5R,7S,9R)-5-[(S)-1′-Hydroxymethylphenyl)]-10,10-dimethyl-4-oxa-6-thiatricyclo[7.1.1.02,7]undecane
C18H24O2SDr >99% (NMR)[α]25D=−45.9Source of chirality: (−)-myrtenalAbsolute configuration: (1S,2R,5R,7S,9R,S)
(S)-(+)-2-Phenylpropane-1,2-diol
C9H12O2Ee >99%[α]23D=+5.7Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(S)-(−)-2-Phenylbutane-1,2-diol
C10H14O2Ee >98%[α]25D=−7.2Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(S)-(−)-3-Methyl-2-phenylbutane-1,2-diol
C11H16O2Ee >98%[α]20D=−19.5Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(S)-(−)-2-Phenylbut-3-ene-1,2-diol
C10H12O2Ee >98%[α]20D=−43.4Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(S)-(+)-2,4-Diphenylbut-3-yne-1,2-diol
C16H14O2Ee >99%[α]20D=+11.0Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(S)-(+)-2,4-Diphenylbutane-1,2-diol
C16H18O2Ee >99%[α]23D=+10.6Source of chirality: asymmetric synthesisAbsolute configuration: (S)
(S)-(+)-1-Phenylethane-1,2-diol
C8H10O2Ee >99%[α]23D=+38.6Source of chirality: asymmetric synthesisAbsolute configuration: (S)
| Lipase-catalyzed asymmetric synthesis of 6-(3-chloro-2-hydroxypropyl)-1,3-dioxin-4-ones and their conversion to chiral 5,6-epoxyhexanoates Tetrahedron: Asymmetry, Volume 2, Issue 5, 1991, Pages 343-346 Jun-ichi Sakaki, Hiroko Sakoda, Yoshiaki Sugita, Masayuki Sato, Chikara Kaneko | ||||
C9H13ClO4 E.e=≥98% [by HPLC analysis (Chiralcell OD)] [α]D20= +19.3 (c 1.67, CHCl3) Source of chirality: kinetic resolution by lipase Absolute configuration R (assigned by conversion to the intermediate of L-carnitine)
(S)-6-(3-Chloro-2-acetoxypropyl)-2,2-dimethyl-1,3-dioxin-4-one
C11H15ClO5 E.e.=≥98% [by HPLC analysis (Chiralcell OJ)] [α]D20 = +0.12 (c 1.20, CHCl3) Source of chirality: Asymmetric acetylation catalyzed by lipase Absolute configuration S (assigned by conversion to the known compound)
(S)-6-Chloro-3-oxohexan-5-olide
C6H7ClO3 E.e.=≥98% [α]D25= −83.4 (c 1.07, MeOH) Source of chirality: from a precursor obtained by enzymatic method Absolute configuration S (assigned by conversion to the known compound)
Methyl (3r,5S)-5,6-Epoxy-3-methoxyhexanoate
C8H14O4 E.e.=≥98% [α]D24= −19.1 (c 3.55, CHCl3) Source of chirality: enzymatic method, asymmetric addition Absolute configuration 3R, 5S
| Enantioselective synthesis of either enantiomer of α-alkyl-α-hydroxy-α-phenylacetic acids using chiral auxiliaries Tetrahedron: Asymmetry, Volume 16, Issue 10, 23 May 2005, Pages 1837-1843 Salvador Pérez-Estrada, Selene Lagunas-Rivera, Marı́a Elena Vargas-Dı́az, Pedro Velázquez-Ponce, Pedro Joseph-Nathan, L. Gerardo Zepeda | ||||
C14H22O2S Dr = >99% (NMR) Source of chirality: (−)-myrtenal Absolute configuration: (1S,2R,5R,7S,9R) = −5.2 (c 0.11, CHCl3)
(1S,2R,5R,7S,9R,1′R)-5-(1′-Hydroxy-1′-phenyl-1′-ethyl)-10,10-dimethyl-4-oxa-6-thia-tricyclo[7.1.1.02,7]undecane
C20H28O2S Dr = >99% (NMR) Source of chirality: (−)-myrtenal Absolute configuration: (1S,2R,5R,7S,9R,1′R) = −46.7 (c 0.28, CHCl3)
(1S,2R,3S,5R,2′S)-6,6-Dimethyl-3-(2′-ethoxy-1′-phenyl-1′-oxo-2′-ethylsulfanyl)-2-hydroxymethyl-bicyclo[3.1.1]heptane
C20H28O3S Dr = >99% (NMR) Source of chirality: (−)-myrtenal Absolute configuration: (1S,2R,3S,5R,2′S) = +81.9 (c 0.71, EtOH)
(1S,2R,3S,5R,2′R)-6,6-Dimethyl-3-(2′-ethoxy-1′-phenyl-1′-oxo-2′-ethylsulfanyl)-2-hydroxymethyl-bicyclo[3.1.1]heptane
C20H28O3S Dr = >99% (NMR) Source of chirality: (−)-myrtenal Absolute configuration: (1S,2R,3S,5R,2′R) = +8.2 (c 0.529, EtOH)
(1S,2R,3S,5R,2′S)-6,6-Dimethyl-3-(-2′-ethoxy-1′-phenyl-1′-oxo-2′-ethylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane
C26H42O3SSi Dr = >99% (NMR) Source of chirality: (−)-myrtenal Absolute configuration:(1S,2R,3S,5R,2′S) = +75.3 (c 0.51, EtOH)
(1S,2R,3S,5R,2′R)-6,6-Dimethyl-3-(2′-ethoxy-1′-phenyl-1′-oxo-2′-ethylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane
C26H42O3SSi Dr = >99% (NMR) Source of chirality: (−)-myrtenal Absolute configuration: (1S,2R,3S,5R,2′R) = −4.4 (c 0.40, CHCl3)
(1S,2R,3S,5R,1′R,2′S)-6,6-Dimethyl-3-(1′-ethoxy-2′-phenyl-2′-hydroxy-1′-propylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane
C27H46O3SSi Dr = >99% (NMR) Source of chirality: (−)-myrtenal Absolute configuration: (1S,2R,3S,5R,1′R,2′S) = +25.6 (c 0.90, CHCl3)
(1S,2R,3S,5R,1′R,2′R)-6,6-Dimethyl-3-(1′-ethoxy-2′-phenyl-2′-hydroxy-1′-propylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane
C27H46O3SSi Dr = >99% (NMR) Source of chirality: (−)-myrtenal Absolute configuration: (1S,2R,3S,5R,1′S,2′R) = −122.4 (c 0.59, CHCl3)
(1S,2R,3S,5R,1′R,2′S)-6,6-Dimethyl-3-(1′-ethoxy-2′-phenyl-2′-hydroxy-1′-butylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane
C28H48O3SSi Dr = >99% (NMR) Source of chirality: (−)-myrtenal Absolute configuration: (1S,2R,3S,5R,1′R,2′S) = +46.2 (c 0.80, CHCl3)
(1S,2R,3S,5R,1′S,2′R)-6,6-Dimethyl-3-(1′-ethoxy-2′-phenyl-2′-hydroxy-1′-butylsulfanyl)-2-(O-t-butyl-dimethylsilyl-hydroxymethyl)-bicyclo[3.1.1]heptane
C28H48O3SSi Dr = >99%(NMR) Source of chirality: (−)-myrtenal Absolute configuration: (1S,2R,3S,5R,1′S,2′R) = +67.8 (c 0.64, CHCl3)
Bis [(1S,2R,3S,5R)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6,6-dimethyl-bicyclo[3.1.1]heptane-3-thiol]
C32H62O2S2Si2 Ee = >99% Source of chirality: (−)-myrtenal Absolute configuration: (1S,2R,3S,5R) = +119.5 (c 0.48, CHCl3)
(R)-(−)-2-Hydroxy-2-phenylbutanal
C10H12O2 Ee = >99% Source of chirality: asymmetric synthesis Absolute configuration: (R) = +13.3 (c 0.23, EtOH)
(S)-(−)-2-Hydroxy-2-phenylpropanoic acid
C9H10O3 Ee = >99% Source of chirality: asymmetric synthesis Absolute configuration: (S) = +37.1 (c 0.50, EtOH)
(S)-(−)-2-Hydroxy-2-phenylbutanoic acid
C10H12O3 Ee = >98% Source of chirality: asymmetric synthesis Absolute configuration: (S) = +31.5 (c 0.6, EtOH)
| Enantioselective total syntheses of the novel tricyclic sesquiterpene hydrocarbons (+)- and (−)-kelsoene. Absolute configuration of the natural product Tetrahedron Letters, Volume 42, Issue 15, 9 April 2001, Pages 2855-2857 Goverdhan Mehta, K Srinivas | ||||
| Determination of the absolute configuration of yessotoxin, a polyether compound implicated in diarrhetic shellfish poisoning, by NMR spectroscopic method using a chiral anisotropic reagent, methoxy-(2-naphthyl)acetic acid Tetrahedron Letters, Volume 37, Issue 39, 23 September 1996, Pages 7087-7090 Haruko Takahashi, Takenori Kusumi, Yukiko Kan, Masayuki Satake, Takeshi Yasumoto | ||||
| Determination of absolute configuration and enantiomeric purity of spirocyclic alcohols by 1h nmr Tetrahedron Letters, Volume 25, Issue 50, 1984, Pages 5801-5804 Kuninobu Kabuto, Fujiko Yasuhara, Shozo Yamaguchi | ||||
| The first enantioselective synthesis of optically pure (R)- and (S)-5,5″-dihydroxy-4′,4 ,7,7″-tetramethoxy-8,8″-biflavone and the reconfirmation of their absolute configurationTetrahedron Letters, Volume 38, Issue 6, 10 February 1997, Pages 1087-1090 Guo-Qiang Lin, Min Zhong | ||||
| Corrigendum to “Convolutamydine A: the first authenticated absolute configuration and enantioselective synthesis”: [Tetrahedron: Asymmetry 17 (2006) 3070] Tetrahedron: Asymmetry, Volume 18, Issue 2, 14 February 2007, Page 298 Giancarlo Cravotto, Giovanni B. Giovenzana, Giovanni Palmisano, Andrea Penoni, Tullio Pilati, Massimo Sisti, Federica Stazi | ||||
| Enantioselective synthesis of (5R,9R)-5-propyl-octahydroindolizine [(−)-gephyrotoxin 167B] Tetrahedron: Asymmetry, Volume 3, Issue 6, June 1992, Pages 695-696 Anne Fleurant, Jean Pierre Célérier, Gérard Lhommet | ||||
C6H13NO E.e.>98%, [α]22D=−8.3 (c=1.94, EtOH) Source of chirality: (S)-pyroglutamic acid (U.C.I.B. France) Absolute configuration: 2(S)
(2R)-1-Benzyloxycarbonyl-2-(4-oxoheptyl)-pyrrolidine
C19H27NO3 E.e.>98%, [α]21D=−47.2 (c=2, EtOH) Source of chirality: (S)-pyroglutamic acid (U.C.I.B. France) Absolute configuration: 2(R) (Assigned by corrrelation with the final product)
(5R,9R)-5-Propyl-octahydroindolizine
C11H21N (−) Gephyrotoxin 167B E.e.>98%, [α]20D=−115 (c=1.17, CH2Cl2) Source of chirality: (S)-pyroglutamic acid (U.C.I.B. France) Absolute configuration: 5(R), 9(R) (Assigned by correlation of specific rotation with literature)
| Enantioselective synthesis of siloxycyclopropanes and of ???-oxocarboxylates by asymmetric catalysis Tetrahedron Letters, Volume 30, Issue 16, 1989, Pages 2079-2082 Thomas Kunz, Hans-Ulrich Reissig | ||||
| Enantioselective synthesis and CD assignment of absolute configuration of (−)-1,3-diphenylpropane-1,3-diol Tetrahedron: Asymmetry, Volume 6, Issue 5, May 1995, Pages 1031-1034 Dario Pini, Alessandro Mandoli, Anna Iuliano, Piero Salvadori | ||||
Asymmetric hydrogenation of (1) in the presence of [RuCl2{(R)-biphemp}] (biphemp = 2,2′-bis(diphenyl phosphino)-6,6′-dimethyl-1, 1′-biphenyl) gives (−)-(2); absolute configuration of (−)-(2) is established from CD spectra of derivative (4).
| A formal and enantioselective synthesis of (−)-serricornin, the sex pheromone of the cigarette beetle (lasioderma serricorne F.) Tetrahedron: Asymmetry, Volume 5, Issue 4, April 1994, Pages 641-648 J. Tércio, B. Ferreira, Jacqueline A. Marques, J. P. Marino | ||||
C10H12SO [α]D= +143 (c=2.0; CHCl3) Source of chirality: (−)-menthyl (S)-p-toluenesulfinate Absolute configuration: R
(R)-(E)-1-ethyl-1-(p-tolylsulfinyl)-1-propene
C12H16SO [α]D= +43.3 (c=2.0; CHCl3) Source of chirality: asymmetric synthesis Absolute configuration: R
(3R,4R)-2,2-dichloro-4-ethyl-3-methyl-p-tolylthio γ-butyrolactone
C14H16SO2Cl2 [α]D= +2.96 (c=3.0; CHCl3) m.p.= 108–110°C Source of chirality: asymmetric synthesis Absolute configuration: R,R
(3R,4R)-4-ethyl-3-methyl-4-p-tolylthio γ-butyrolactone
C14H18SO2 [α]D= +66.5 (c=2.3; CHCl3) Source of chirality: asymmetric synthesis Absolute configuration: R,R
(3S,4S)-4-ethyl-3-methyl- γ-butyrolactone
C7H12O2 [α]D= +34.4 (c=2.0; CHCl3) Source of chirality: asymmetric synthesis Absolute configuration: S,S
(3R,4R)-3-methyl-1,4-hexanediol
C7H16O2 [α]D= +12.5(c=1.0; CHCl3) Source of chirality: asymmetric synthesis Absolute configuration: R,R
| Preparation and assignment of configuration of 1-benzoyl- (2S)-tert-butyl-3-methyl-perhydropyrimidin-4-one. Useful starting material for the enantioselective synthesis of α-substituted β-amino acids Tetrahedron: Asymmetry, Volume 3, Issue 6, June 1992, Pages 723-726 Eusebio Juaristi, Delia Quintana | ||||
C15H18N2O2 [α]D29 = + 564.5 (c=1.00, CHCl3) Source of chirality: (S)-asparagine Absolute configuration: 2(S)
1-Benzoyl-2(S)-tert-butyl-3-methyl-2,3-dihydro-4(1H)-pyrimidinone
C16H20N2O2 [α]D29 = + 556 (c=1,00, CHCl3) Source of chirality: (S)-asparagine Absolute configuration: 2(S)
1-Benzoyl-2(S)-tert-butyl-3-methyl-perhydropyrimidin-4-one
C16H22N2O2 [α]D29 = + 50 (c=1.00, CHCl3) Source of chirailty: (S)-asparagine Absolute configuration: 2(S)
1-Benzoyl-2(S)-tert-butyl-3-methyl-5(R)-methyl-perhydropyrimidin-4-one
C17H24N2O2 [α]D29 = + 37 (c=1.00, CHCl3) Source of chirailty: (S)-asparagine Absolute configuration: 2(S),5(R)
| Highly enantioselective synthesis of a Corey prostaglandin intermediate Tetrahedron: Asymmetry, Volume 3, Issue 1, 1992, Pages 115-122 Baptiste Ronan, Henri B. Kagan | ||||
C22H24OS [α]25D = −121.4 (c= 0.98, acetone) 100 % ee Absolute configuration: 1R, 2S, 4S, 7R by chemical correlation to the norbornenone below
Bicyclo [2.2.1.] hept-7-benzyloxymethyl-5-ene-2-one
C15H16O2 [α]25D = −454 (c= 1.03, CHCl3) 100 % ee and absolute configuration 1R, 4S, 7R by comparison to lit.value.
Ethoxy p-tolyl vinyl sulfonium tetrafluoroborate
C11H15OSBF4 from (R)-(+)- p-tolyl vinyl sulfoxide (100 % ee) [α]25D = + 59 (c=1, CHCl3) 100 % ee Absolute configuration: RS
Bicyclo [2.2.1.] hept-7-benzyloxymethyl-5-ene-2-p-tolyl-sulfinyl
C22H24O2S [α]25D = −181.5 (c= 1.11, acetone) 100 % ee Absolute configuration: 1R, 2S, 4S, 7R, SS (by chemical correlation)
| Synthesis of enantiopure bis-isoxazolines from (4R)-(+)-4-acetoxycyclopent-2-enone Tetrahedron: Asymmetry, Volume 12, Issue 4, 19 March 2001, Pages 619-623 Giorgio Adembri, M. Laura Paoli, Patrizia Rossi, Alessandro Sega | ||||
C12H7Cl2NO2 Ee=100% [α]D20=+347.6 (c=0.3, CHCl3) Source of chirality: (1R,4S)-(+)-cyclopentene-1,3-diol 1-acetate and enantioselective synthesis Absolute configuration: (3aS,6aR)
(3aS,4aS,7aR,7bR)-(+)-3,5-Di(2,6-dichlorophenyl)-4H-[1,2]oxazolo[5′,4′:3,4]cyclopenta[d][1,2]oxazol-4-one
C19H10Cl4N2O3 Ee=100% [α]D20=+362.3 (c=0.6, CHCl3) Source of chirality: (1R,4S)-(+)-cyclopentene-1,3-diol 1-acetate and enantioselective synthesis Absolute configuration: (3aS,4aS,7aR,7bR)
(3aS,3bS,6aS,7aS)-(+)-3,6-Di(2,6-dichlorophenyl)-7H-[1,2]oxazolo[5′,4′:3,4]cyclopenta[d][1,2]oxazol-7-one
C19H10Cl4N2O3 Ee=100% [α]D20=+428.6 (c=0.03, CHCl3) Source of chirality: (1R,4S)-(+)-cyclopentene-1,3-diol 1-acetate and enantioselective synthesis Absolute configuration: (3aS,3bS,6aS,7aS)
(3aS,6R,6aR)-(+)-3-(2,6-Dichlorophenyl)-4-oxo-4,5,6,6a-tetrahydro-3aH-cyclopent[d]isoxazol-6-yl acetate
C14H11Cl2NO4 Ee=100% [α]D20=+319.5 (c=0.3, CHCl3) Source of chirality: (1R,4S)-(+)-cyclopentene-1,3-diol 1-acetate and enantioselective synthesis Absolute configuration: (3aS,6R,6aR)
| Enantioselective synthesis of cyclohexene nitroaldehydes Tetrahedron Letters, Volume 30, Issue 24, 1989, Pages 3179-3182 M. Ch. Moreno, J. Plumet, E. Román, J. A. Serrano, M. L. Rodríguez and, C. Ruiz-Pérez | ||||
| Alicyclic β-amino acids: useful synthons in drug research Il Farmaco, Volume 55, Issue 3, March 2000, Pages 181-183 Ferenc Fülöp | ||||
| Enantioselective synthesis of the volatile anesthetic desflurane Tetrahedron: Asymmetry, Volume 8, Issue 18, 25 September 1997, Pages 3023-3025 Leonid A. Rozov, Chialang G. Huang, Donald F. Halpern, Gerald G. Vernice, Keith Ramig | ||||
| Camphor-based oxazaphospholanes as chiral templates for the enantioselective synthesis of α-chlorophosphonic acids Tetrahedron: Asymmetry, Volume 10, Issue 22, 19 November 1999, Pages 4277-4280 Giovanni Battista Giovenzana, Roberto Pagliarin, Giovanni Palmisano, Tullio Pilati, Massimo Sisti | ||||
| Enantioselective synthesis of 3-demethoxyaranciamycinone via asymmetric epoxidation Tetrahedron Letters, Volume 25, Issue 23, 1984, Pages 2463-2466 Erwin Broser, Karsten Krohn, Klaus Hintzer and, Volker Schurig | ||||
| Asymmetric, catalytic, vinylogous aldol reactions using pyrrole-based dienoxy silanes. Enantioselective synthesis of α,β-unsaturated γ-butyrolactam synthons Tetrahedron Letters, Volume 50, Issue 26, 1 July 2009, Pages 3428-3431 Claudio Curti, Andrea Sartori, Lucia Battistini, Gloria Rassu, Franca Zanardi, Giovanni Casiraghi | ||||
| Synthesis of 22-oxaspiro[4.5]decane CD-ring modified analogs of 1α,25-dihydroxyvitamin D3 Tetrahedron Letters, Volume 50, Issue 28, 15 July 2009, Pages 4174-4177 Frederik De Buysser, Lieve Verlinden, Annemieke Verstuyf, Pierre J. De Clercq | ||||
| Enantioselective synthesis of the lactone moiety of HMG-CoA reductase inhibitor: stereoselective synthesis of (+)-(4R,6R)-4-hydroxy-6-(2-phenylethyl)-tetrahydro-2H-pyran-2-one Tetrahedron: Asymmetry, Volume 8, Issue 2, 23 January 1997, Pages 181-184 Toshio Honda, Satoko Ono, Hirotake Mizutani, Keith O. Hallinan | ||||
| Enantioselective synthesis and absolute configurations of the enantiomers of o-carboranylalanine Tetrahedron Letters, Volume 41, Issue 5, 29 January 2000, Pages 751-754 Peter Lindström, Charlotta Naeslund, Stefan Sjöberg | ||||
| Convenient enantioselective synthesis of β-trifluoromethyl-β-aminoketones by organocatalytic asymmetric Mannich reaction of aryl trifluoromethyl ketimines with acetone Tetrahedron: Asymmetry, Volume 19, Issue 6, 3 April 2008, Pages 761-764 Volodymyr A. Sukach, Nataliya M. Golovach, Volodymyr V. Pirozhenko, Eduard B. Rusanov, Mykhaylo V. Vovk | ||||
C11H12F3NO Ee = 80% Chiral source: (S)-proline Absolute configuration: (S) (c 1.80, MeOH)
4-Amino-4-(4-methylphenyl)-5,5,5-trifluoro-2-pentanone
C12H14F3NO Ee = 74% Chiral source: (S)-proline Absolute configuration: (S) (c 0.75, MeOH)
4-Amino-4-(3-methylphenyl)-5,5,5-trifluoro-2-pentanone
C12H14F3NO Ee = 92% Chiral source: (S)-proline Absolute configuration: (S) (c 0.81, MeOH)
4-Amino-4-(4-methoxyphenyl)-5,5,5-trifluoro-2-pentanone
C12H14F3NO2 Ee = 78% Chiral source: (S)-proline Absolute configuration: (S) (c 0.39, MeOH)
4-Amino-4-(4-fluorophenyl)-5,5,5-trifluoro-2-pentanone
C11H12F4NO Ee = 83% Chiral source: (S)-proline Absolute configuration: (S) (c 0.63, MeOH)
| Chemoenzymatic enantioselective synthesis of the polypropionate acid moiety of dolabriferol Tetrahedron: Asymmetry, Volume 14, Issue 17, 5 September 2003, Pages 2567-2571 Robert Chênevert, Gabriel Courchesne, Dave Caron | ||||
C15H30O4SiEe=97%[α]D22=+20.4 (c 2.45, CHCl3)Source of chirality: enzymatic desymmetrizationAbsolute configuration: 2R,3R,4S
(2S,3S,4S)-5-Acetoxy-3-(tert-butyldimethylsiloxy)-2,4-dimethyl-1-pentanal
C15H30O4SiEe=97%[α]D22=+17.5 (c 1.85, CHCl3)Source of chirality: enzymatic desymmetrizationAbsolute configuration: 2S,3S,4S
(2S,3S,4R,5S)-3-(tert-Butyldimethylsiloxy)-2,4-dimethyl-1,5-heptanediol
C15H34O3SiEe=97%[α]D22=−7.4 (c 2.19, C6H6)Source of chirality: enzymatic desymmetrizationAbsolute configuration: 2S,3S,4R,5S
(2S,3S,4R,5R)-3-(tert-Butyldimethylsiloxy)-2,4-dimethyl-1,5-heptanediol
C15H34O3SiEe=97%[α]D22=−2.5 (c 1.90, C6H6)Source of chirality: enzymatic desymmetrizationAbsolute configuration: 2S,3S,4R,5R
(2R,3S,4S)-3-(tert-Butyldimethylsiloxy)-2,4-dimethyl-5-oxoheptanal
C15H30O3SiEe=97%[α]D22=−5.9 (c 2.47, C6H6)Source of chirality: enzymatic desymmetrizationAbsolute configuration: 2R,3S,4S
| Synthesis and absolute configuration of polypropionate metabolites of siphonaria australis Tetrahedron Letters, Volume 33, Issue 4, 1992, Pages 437-440 Uma N. Sundram, Kim F. Albizati | ||||
| Synthesis of 6-deoxy-homoDMDP and its C(5)-epimer: absolute stereochemistry of natural products from Hyacinthus orientalis Tetrahedron: Asymmetry, Volume 13, Issue 2, 28 February 2002, Pages 111-113 Jean-Bernard Behr, Georges Guillerm | ||||
C7H15NO4 [α]D20=+46.0 (c=1.15, H2O) Source of chirality: Absolute configuration: 2R,3R,4R,5R-xylose
2,5-Imino-2,5,6-trideoxy-
C7H15NO4 [α]D20=+37.9 (c=1.8, H2O) Source of chirality: Absolute configuration: 2R,3R,4R,5S-xylose
| An enantioselective synthesis of nitrogen protected 3-arylserine esters Tetrahedron: Asymmetry, Volume 15, Issue 22, 15 November 2004, Pages 3485-3487 Lisa H. Bourdon, David J. Fairfax, Gregory S. Martin, Casey J. Mathison, Pavel Zhichkin | ||||
C16H23NO5 Ee = 85% Source of chirality: asymmetric synthesis Absolute configuration: (2R,3S) (c 1.1, EtOH)
Ethyl (2R,3S)-2-tert-butoxycarbonylamino-3-hydroxy-3-(3-trifluoromethylphenyl)propionate
C17H22F3NO5 Ee = 81% Source of chirality: asymmetric synthesis Absolute configuration: (2R,3S) (c 0.5, EtOH)
Ethyl (2R,3S)-2-tert-butoxycarbonylamino-3-hydroxy-3-(4-nitrophenyl)propionate
C16H22N2O7 Ee = 84% Source of chirality: asymmetric synthesis Absolute configuration: (2R,3S) (c 0.5, EtOH)
Ethyl (2R,3S)-2-tert-butoxycarbonylamino-3-hydroxy-3-(2-furyl)propionate
C14H21NO6 Ee = 42% Source of chirality: asymmetric synthesis Absolute configuration: (2R,3S) (c 0.5, EtOH)
Ethyl (2R,3S)-2-tert-butoxycarbonylamino-3-hydroxy-3-(3-methoxyphenyl)propionate
C17H25NO6 Ee = 83% Source of chirality: asymmetric synthesis Absolute configuration: (2R,3S) (c 0.5, EtOH)
Ethyl (2R,3S)-2-tert-butoxycarbonylamino-3-hydroxy-3-(4-chlorophenyl)propionate
C16H22ClNO5 Ee = 84% Source of chirality: asymmetric synthesis Absolute configuration: (2R,3S) (c 0.5, EtOH)
Ethyl(2R,3S)-2-tert-butoxycarbonylamino-3-hydroxy-3-(3,4-methylenedioxyphenyl)phenylpropionate
C17H23NO7 Ee = 87% Source of chirality: asymmetric synthesis Absolute configuration: (2R,3S) (c 0.5, EtOH)
Ethyl (2R,3S)-2-tert-butoxycarbonylamino-3-hydroxy-3- 4-(2-phthalimido)ethoxy phenylpropionate
C26H30N2O8 Ee = 85% Source of chirality: asymmetric synthesis Absolute configuration: (2R,3S) (c 1.1, EtOH)
| Enantioselective synthesis of (R)-and (S)-α-aminoacids using (6S)- and (6R)-6-methyl-morpholine-2,5-dione derivatives Tetrahedron: Asymmetry, Volume 7, Issue 1, 1996, Pages 189-196 Gianni Porzi, Sergio Sandri | ||||
[α]25D= −254.7 (c=0.55,chloroform)
Source of chirality : from (S)-phenethylamine
Absolute configuration : 3R,6S assigned by 1H-NMR
C16H21NO3
(3R,6S)-4-N((S)-1-phenethyl)-3-benzyl-6-methyl-1,4-morpholin-2,5-dione [α]25D= −19.6 (c=2.13, chloroform) Source of chirality : from (S)-phenethylamine Absolute configuration : 3R,6S assigned by 1H-NMR C20H21NO3
(3S,6R)-4-N((S)-1-phenethyl-3,6-dimethyl-1,4-morpholin-2,5-dione [α]25D=42.2 (c=0.64, chloroform) Source of chirality : from (S)-phenethylamine Absolute configuration : 3S,6R assigned by 1H-NMR C14H17NO3
(6S)-4N-((S)-1-phenethyl)-6-methyl-1,4-morpholin-2,5-dione mp 118-9°C [α]25D= −199.4 (c=2.05, chloroform) Source of chirality : from (S)-phenethylamine Absolute configuration : 6S assigned by 1H-NMR C13H15NO3
(6R)-4N-((S)-1-phenethyl)-6-methyl-1,4-morpholin-2,5-dione mp 98–9°C [α]25D= −106.8 (c=2.25.chloroform) Source of chirality : from (S)-phenethylamine Absolute configuration : 6S assigned by 1H-NMR C13H15NO3
(3R,6S)-4-N-((S)-1-phenethyl)-3,6-dimethyl-1,4-morpholin-2,5-dione [α]25D= −290.7 (c=1.08,chloroform) Source of chirality : from (S)-phenethylamine Absolute configuration : 3R,6S assigned by 1H-NMR C14H17NO3
(3S,6R)-4-N-((S)-1-phenethyl)-3-propyl-6-methyl-1,4-morpholin-2,5-dione [α]25D=49.4 (c=0.84,chloroform) Source of chirality : from (S)-phenethylamine Absolute configuration : 3S,6R assigned by 1H-NMR C16H21NO3
(3S,6R)-4-N-((S)-1-phenethyl)-3-benzyl-6-methyl-1,4-morpholin-2,5-dione [α]25D=54.1 (c=2.27,chloroform) Source of chirality : from (S)-phenethylamine Absolute configuration : 3S,6R assigned by 1H-NMR C20H21NO3
| Novel, enantioselective synthesis of vicinal cyclohexane-diamines as key-intermediates for highly selective opioid kappa and sigma agonists. Tetrahedron: Asymmetry, Volume 3, Issue 3, 1992, Pages 329-332 Wolfgang H. Schlichter, August W. Frahm | ||||
C13H18N2O E.e. = >99 % (det. by Mosher-derivatives) αD = + 20.2 (c = 1.08 g/100ml in EtOH) mp. = 142–145δC Source of chirality:1S-Methyl-benzylamine Absolute configuration:1S,2R
(1S,2S)-2-Benzamido-cyclohexanamin
C13H18N2O E.e. = > 99 % (det. by Mosher-derivatives) αD = +54.3 (c = 0.53 g/100ml in EtOH) mp. = 187–189 °C Source of chirality:1S-Methyl-benzylamine Absolute configuration:1S,2S
(1S,2R)-2-Benzamido-(N-1′S-Methyl-benzylamino)-cyclohexanamin-hydrochlorid
C21H27ClN2O E.e. = >99% (det. by Mosher-derivatives) αD = −70.5 (c =0.62 g/100ml in EtOH) mp. = 188–191 °C Source of chirality:1S-Methyl-benzylamine Absolute configuration:1S,2R,1′S
(1S,2S)-2-Benzamido-(N-1′S-Methyl-benzylamino)-cyclohexanamin-hydrochlorid
C21H27ClN2O E.e. = >99% (det. by Mosher-derivatives) αD = −7.0 (c = 0.52 g/100ml in EtOH) mp. = 190–193°C Source of chirality:1S-Methyl-benzylamine Absolute configuration:1S,2S,1′S
(1S,2R)-2-Methoxy-N-Acetyl-cyclohexanamin
C9H17NO2 E.e. = > 99 % (det. by Masher-derivative) αD22 = −79.6 (c = 1.0 g/100ml in EtOH) mp. =99−101°C Source of chirality:1S-Methyl-benzylamine Absolute configuration:1S,2R
(1S,2R)-Hydroxy-N-Acetyl-cyclohexanamin
C8H15NO2 E.e. = > 99% (det. by Mosher-derivatives) αD22 =−31.6 (c =0.48 g/100ml in EtOH) mp. = 126–127 °C Source of chirality:1S-Methyl-benzylamine Absolute configuration:1S,2R
(1S,2R)-2-Methansulfonato-N-Acetyl-cyclohexanamin
C9H17NO4S E.e. = > 99 % (det. by Mosher-derivatives) αD22 =−98.1 (c =0.42 g/100ml in EtOH) mp. = 126–128 °C Source of chirality:1S-Methyl-benzylamine Absolute configuration:1S,2R
(1S,2S)-(1-Pyrrolidino)-N-Acetyl-cyclohexanamin
C12H22N2O E.e. = >99% (det. by Mosher-derivatives) αD22 = +26.7 (c =0.50 g/100ml in EtOH) mp. =113–115°C Source of chirality:1S-Methyl-benzylamine Absolute configuration:1S,2S
| Enantioselective synthesis of bridgehead hydroxyl bicyclo[2.2.2]octane derivatives via asymmetric allylindation Tetrahedron: Asymmetry, Volume 17, Issue 3, 6 February 2006, Pages 410-415 Viveca Thornqvist, Sophie Manner, Torbjörn Frejd | ||||
C11H18O3 Ee = 78% Source of chirality: asymmetric synthesis Absolute configuration: (7S) (c 1.66, EtOH)
(−)-7-(2-Methyl-allyl)-1,4-dioxaspiro[4.5]decane-7-ol
C12H20O3 Ee = 71% Source of chirality: asymmetric synthesis Absolute configuration: not determined (c 0.90, CHCl3)
(−)-7-Allyl-1,4-dithiaspiro[4.5]decane-7-ol
C11H18OS2 Ee = 54% Source of chirality: asymmetric synthesis Absolute configuration: not determined (c 1.30, CHCl3)
(−)-7-(2-Methyl-allyl)-1,4-dithiaspiro[4.5]decane-7-ol
C12H20OS2 Ee = 23% Source of chirality: asymmetric synthesis Absolute configuration: not determined (c 1.08, CHCl3)
(−)-1-Allyl-3,3-dimethyl-cyclohexanol
C11H20O Ee = 37% Source of chirality: asymmetric synthesis Absolute configuration: not determined (c 1.13, CHCl3)
(+)-3,3-Dimethyl-1-(2-methyl-allyl)-cyclohexanol
C12H22O Ee = 38% Source of chirality: asymmetric synthesis Absolute configuration: not determined (c 1.32, CHCl3)
(−)-(7R)-(7-Allyl-1,4-dioxaspiro[4.5]dec-7-yloxy)-tert-butyl-dimethyl silane
C17H32O3Si Ee = 79% Source of chirality: asymmetric synthesis Absolute configuration: (7R) (c 1.11, EtOH)
(+)-(7S)-(7-Allyl-1,4-dioxaspiro[4.5]dec-7-yloxy)-tert-butyl-dimethyl-silane
C17H32O3Si Ee = 78% Source of chirality: asymmetric synthesis Absolute configuration: (7S) (4.09, EtOH)
(+)-(3R)-3-Allyl-3-(tert-butyl-dimethyl-silyloxy)-cyclohexanone
C15H28O2Si Ee = 79% Source of chirality: asymmetric synthesis Absolute configuration: (3R) (c 1.30, EtOH)
(+)-(1R,4R,6S)-exo-4-(tert-Butyl-dimethyl-silyloxy)-6-hydroxy-bicyclo[2.2.2]octan-2-one
C14H26O3Si Ee = 79% Source of chirality: asymmetric synthesis Absolute configuration: (1R,4R,6S) (c 1.09, EtOH)
(+)-(1S,4S,6R)-endo-4-(tert-Butyl-dimethyl-silyloxy)-6-hydroxy-bicyclo[2.2.2]octan-2-one
C14H26O3Si Ee = >98% Source of chirality: asymmetric synthesis Absolute configuration: (1S,4S,6R) (c 1.01, EtOH)
| 1,3-Dipolar cycloadditions of azomethine ylides with chiral acrylates derived from methyl (S)- and (R)-lactate: diastereo- and enantioselective synthesis of polysubstituted prolines Tetrahedron: Asymmetry, Volume 17, Issue 13, 14 August 2006, Pages 1985-1989 Carmen Nájera, M. de Gracia Retamosa, José M. Sansano | ||||
C17H21NO6 [α]D = −82.6 (c 1, CHCl3) Source of chirality: methyl (S)-lactate Absolute configuration: (1′S,2R,4R,5S)
2-Isopropyl 4-[(1S)-1-(methoxycarbonyl)-1-methyl] (2R,4R,5S)-5-phenylpyrrolidine-2,4-dicarboxylate
C19H25NO6 [α]D = −63.0 (c 1, CHCl3) Source of chirality: methyl (S)-lactate Absolute configuration: (1′S,2R,4R,5S)
2-tert-Butyl 4-[(1S)-1-(methoxycarbonyl)-1-methyl] (2R,4R,5S)-5-phenylpyrrolidine-2,4-dicarboxylate
C20H27NO6 [α]D = −59.8 (c 1, CHCl3) Source of chirality: methyl (S)-lactate Absolute configuration: (1′S,2R,4R,5S)
4-[(1S)-1-(Methoxycarbonyl)-1-methyl] 2-methyl (2R,4R,5S)-5-(2-naphthyl)pyrrolidine-2,4-dicarboxylate
C21H23NO6 [α]D = −63.9 (c 1.2, CHCl3) Source of chirality: methyl (S)-lactate Absolute configuration: (1′S,2R,4R,5S)
2-tert-Butyl 4-[(1S)-1-(methoxycarbonyl)-1-methyl] (2R,4R,5S)-5-(2-naphthyl)pyrrolidine-2,4-dicarboxylate
C24H29NO6 [α]D = −57.0 (c 1, CHCl3) Source of chirality: methyl (S)-lactate Absolute configuration: (1′S,2R,4R,5S)
4-[(1S)-1-(Methoxycarbonyl)-1-methyl] 2-methyl (2R,4R,5S)-2-methyl-5-phenylpyrrolidine-2,4-dicarboxylate
C18H23NO6 [α]D = −66.3 (c 1.2, CHCl3) Source of chirality: methyl (S)-lactate Absolute configuration: (1′S,2R,4R,5S)
2-tert-Butyl 4-[(1S)-1-(methoxycarbonyl)-1-methyl] (2R,4R,5S)-2-methyl-5-phenylpyrrolidine-2,4-dicarboxylate
C21H29NO6 [α]D = −57.4 (c 1, CHCl3) Source of chirality: methyl (S)-lactate Absolute configuration: (1′S,2R,4R,5S)
4-[(1S)-1-(Methoxycarbonyl)-1-methyl] 2-methyl (2R,4R,5S)-2-isobutyl-5-phenylpyrrolidine-2,4-dicarboxylate
C21H29NO6 [α]D = −44.0 (c 1.2, CHCl3) Source of chirality: methyl (S)-lactate Absolute configuration: (1′S,2R,4R,5S)
4-[(1S)-1-(Methoxycarbonyl)-1-methyl] 2-methyl (2S,4R,5S)-2-benzyl-5-phenylpyrrolidine-2,4-dicarboxylate
C24H27NO6 [α]D = −45.3 (c 1, CHCl3) Source of chirality: methyl (S)-lactate Absolute configuration: (1′S,2S,4R,5S)
| Asymmetric aminohydroxylation of vinyl indoles: a short enantioselective synthesis of the bisindole alkaloids dihydrohamacanthin A and dragmacidin A Tetrahedron: Asymmetry, Volume 13, Issue 4, 22 March 2002, Pages 383-394 Cai-Guang Yang, Jun Wang, Xiao-Xia Tang, Biao Jiang | ||||
C25H23BrN2O5S E.e.=80% [α]D20=+29 (c 0.59, CHCl3) Source of chirality: asymmetric synthesis Absolute configuration: S
Phenylmethyl (1S)-N-[2-[6-bromo-1-(4-methylphenyl)sulfonyl]-1H-indol-3-yl]-2-hydroxy]ethylcarbamate
C25H23BrN2O5S E.e.=24% [α]D20=+8 (c 0.53, CHCl3) Source of chirality: asymmetric synthesis Absolute configuration: S
1,1-Dimethylethyl (1S)-N-[1-[6-bromo-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl]-2-hydroxy]ethylcarbamate
C22H25BrN2O5S E.e.=94% [α]D20=+47 (c 0.38, CHCl3) Source of chirality: asymmetric synthesis Absolute configuration: S
1,1-Dimethylethyl (1S)-N-[2-[6-bromo-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl]-2-hydroxy]ethylcarbamate
C22H25BrN2O5S E.e.=17% [α]D20=+9 (c 0.30, CHCl3) Source of chirality: asymmetric synthesis Absolute configuration: S
1,1-Dimethylethyl (1S)-N-[1-[(4-methylphenyl)sulfonyl-1H-indol-3-yl]-2-hydroxy]ethylcarbamate
C22H26N2O5S E.e.=86% [α]D20=+38.6 (c 1.25, CHCl3) Source of chirality: asymmetric synthesis Absolute configuration: S
1,1-Dimethylethyl (1S)-N-[2-[4-methylphenyl)sulfonyl]-1H-indol-3-yl]-2-hydroxy]ethylcarbamate
C22H26N2O5S E.e.=42% [α]D20=+11.8 (c 1.20, CHCl3) Source of chirality: asymmetric synthesis Absolute configuration: S
1,1-Dimethylethyl (1S)-N-[1-[5-methoxyl-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl]-2-hydroxy]ethylcarbamate
C23H28N2O6S E.e.=75% [α]D20=+22 (c 0.85, CHCl3) Source of chirality: asymmetric synthesis Absolute configuration: S
1,1-Dimethylethyl (1S)-N-[2-[5-methoxyl-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl]-2-hydroxy]ethylcarbamate
C23H28N2O6S E.e.=3% [α]D20=+2.5 (c 1.675, CHCl3) Source of chirality: asymmetric synthesis Absolute configuration: S
1,1-Dimethylethyl (1S)-N-[1-[5-bromo-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl]-2-hydroxy]ethylcarbamate
C22H25BrN2O5S E.e.=69% [α]D20=+7.8 (c 1.90, CHCl3) Source of chirality: asymmetric synthesis Absolute configuration: S
1,1-Dimethylethyl (1S)-N-[2-[5-bromo-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl]-2-hydroxy]ethylcarbamate
C22H25BrN2O5S E.e.=12% [α]D20=+4.8 (c 1.50, CHCl3) Source of chirality: asymmetric synthesis Absolute configuration: S
1,1-Dimethylethyl (1S)-N-[1-[6-bromo-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl]-2-[(4-methylphenyl)sulfonyl]oxy]ethylcarbamate
C29H31BrN2O7S2 [α]D20=+15 (c 0.32, CHCl3) Source of chirality: asymmetric synthesis Absolute configuration: S
1,1-Dimethylethyl (1S)-N-[1-[6-bromo-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl]-2-azido]ethylcarbamate
C22H24BrN5O4S [α]D20=+4 (c 1.67, CHCl3) Source of chirality: asymmetric synthesis Absolute configuration: S
(S)-6-Bromo-N-[2-azido-1-[(6-bromo-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl]ethyl]-α-oxoindole-3-acetamide
C27H20Br2N6O4S [α]D20=+45 (c 0.40, CHCl3) Source of chirality: asymmetric synthesis Absolute configuration: S
(S)-3-(6-Bromo-1H-indol-3-yl)-6-[6-bromo-1-[(4-methylphenyl)sulfonyl]-1H-indol-3-yl]-5,6-dihydro-1H-pyrazin-2-one
C27H20Br2N4O3S [α]D20=−27 (c 0.5, acetone) Source of chirality: asymmetric synthesis Absolute configuration: S
Hamacanthin A
C20H14Br2N4O [α]D20=+82 (c 0.135, CH3OH) Source of chirality: asymmetric synthesis Absolute configuration: S
(3S,6S)-3-(6-Bromo-1H-indol-3-yl)-6-[6-bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-piperazin-2-one
C27H22Br2N4O3S [α]D20=−35 (c 1.50, CHCl3) Source of chirality: asymmetric synthesis Absolute configuration: 3S,6S
(3R,6S)-3-(6-Bromo-1H-indol-3-yl)-6-[6-bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-piperazin-2-one
C27H22Br2N4O3S [α]D20=+16 (c 0.42, CHCl3) Source of chirality: asymmetric synthesis Absolute configuration: 3R,6S
(3S,6S)-3,6-Bis(6-bromo-1H-indol-3-yl)piperazin-2-one
C20H16Br2N4O [α]D20=−8 (c 0.17, CH3OH) Source of chirality: asymmetric synthesis Absolute configuration: 3S,6S
(3R,6S)-3,6-Bis(6-bromo-1H-indol-3-yl)piperazin-2-one
C20H16Br2N4O [α]D20=−6 (c 0.275, CH3OH/acetone=1:1) Source of chirality: asymmetric synthesis Absolute configuration: 3R,6S
1,1-Dimethylethyl (6S)-3-[6-bromo-1-(tert-butyloxycarbonyl)-1H-indol-3-yl]-6-[6-bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-5,6-dihydro-2-oxo-1H-pyrazine-1-carboxylate
C37H36Br2N4O7S [α]D20=−70 (c 0.68, CHCl3) Source of chirality: asymmetric synthesis Absolute configuration: S
(6S)-3-[6-Bromo-1-(tert-butyloxycarbonyl)-1H-indol-3-yl]-6-[6-bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-5,6-dihydro-1H-pyrazin-2-one
C32H28Br2N4O5S [α]D20=+94 (c 0.64, CHCl3) Source of chirality: asymmetric synthesis Absolute configuration: S
(6S)-3-[6-Bromo-1-(tert-butyloxycarbonyl)-1H-indol-3-yl]-6-[6-bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-5,6-dihydro-1-methyl-1H-pyrazin-2-one
C33H30Br2N4O5S [α]D20=−26 (c 0.55, CHCl3) Source of chirality: asymmetric synthesis Absolute configuration: S
(6S)-3-(6-Bromo-1H-indol-3-yl)-6-[6-bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-5,6-dihydro-1-methyl-1H-pyrazin-2-one
C28H22Br2N4O3S [α]D20=−115 (c 0.74, CHCl3) Source of chirality: asymmetric synthesis Absolute configuration: S
(3S,6S)-3-(6-Bromo-1H-indol-3-yl)-6-[6-bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-1-methylpiperazin-2-one
C28H24Br2N4O3S [α]D20=−49 (c 0.77, CH3Cl) Source of chirality: asymmetric synthesis Absolute configuration: 3S,6S
(3R,6S)-3-(6-Bromo-1H-indol-3-yl)-6-[6-bromo-1-(toluene-4-sulfonyl)-1H-indol-3-yl]-1-methylpiperazin-2-one
C28H24Br2N4O3S [α]D20=+12 (c 0.20, CH3OH/acetone=1:1) Source of chirality: asymmetric synthesis Absolute configuration: 3R,6S
(3S,6S)-3,6-Bis(6-bromo-1H-indol-3-yl)-1-methylpiperazin-2-one
C21H18Br2N4O [α]D20=−29 (c 0.37, CH3OH/acetone=1:1) Source of chirality: asymmetric synthesis Absolute configuration: 3S,6S
(3R,6S)-3,6-Bis(6-bromo-1H-indol-3-yl)-1-methylpiperazin-2-one
C21H18Br2N4O [α]D20=−32 (c 0.20, CH3OH) Source of chirality: asymmetric synthesis Absolute configuration: 3R,6S
Dragmacidin A
C21H20Br2N4 [α]20D=+4 (c 0.20, CHCl3) Source of chirality: asymmetric synthesis Absolute configuration: 3R,6S
| Enantioselective synthesis of naphthopyran derivatives catalyzed by bifunctional thiourea-tertiary amines Tetrahedron: Asymmetry, Volume 19, Issue 6, 3 April 2008, Pages 709-714 Xiao-Sheng Wang, Gao-Sheng Yang, Gang Zhao | ||||
C20H14N2O Ee = 68% Source of chirality: asymmetric synthesis Absolute configuration: (S) (c 1.15, DMSO)
(S)-3-Amino-1-(4-bromophenyl)-1H-benzo[f]chromene-2-carbonitrile
C20H13BrN2O Ee = 71% Source of chirality: asymmetric synthesis Absolute configuration: (S) (c 0.93, DMSO)
(S)-3-Amino-1-(4-chlorophenyl)-1H-benzo[f]chromene-2-carbonitrile
C20H13ClN2O Ee = 84% Source of chirality: asymmetric synthesis Absolute configuration: (S) (c 0.7, DMSO)
(S)-3-Amino-1-(4-fluorophenyl)-1H-benzo[f]chromene-2-carbonitrile
C20H13FN2O Ee = 90% Source of chirality: asymmetric synthesis Absolute configuration: (S) (c 0.64, DMSO)
(S)-3-Amino-1-p-tolyl-1H-benzo[f]chromene-2-carbonitrile
C21H16N2O Ee = 79% Source of chirality: asymmetric synthesis Absolute configuration: (S) (c 3.05, DMSO)
(S)-3-Amino-1-(4-nitrophenyl)-1H-benzo[f]chromene-2-carbonitrile
C20H13N3O3 Ee = 65% Source of chirality: asymmetric synthesis Absolute configuration: (S) (c 0.4, DMSO)
(S)-3-Amino-1-(4-methoxyphenyl)-1H-benzo[f]chromene-2-carbonitrile
C21H16N2O2 Ee = 62% Source of chirality: asymmetric synthesis Absolute configuration: (S) (c 0.65, DMSO)
(S)-3-Amino-1-(2,4-dichlorophenyl)-1H-benzo[f]chromene-2-carbonitrile
C20H13Cl2N2O Ee = 56% Source of chirality: asymmetric synthesis Absolute configuration: (S) (c 0.73, DMSO)
(S)-3Amino-1-(3-fluorophenyl)-1H-benzo[f]chromene-2-carbonitrile
C20H13FN2O Ee = 70% Source of chirality: asymmetric synthesis Absolute configuration: (S) (c 0.62, DMSO)
(S)-3-Amino-1-(3-methoxyphenyl)-1H-benzo[f]chromene-2-carbonitrile
C21H16N2O2 Ee = 76% Source of chirality: asymmetric synthesis Absolute configuration: (S) (c 0.77, DMSO)
(S)-3-Amino-1-(2-chlorophenyl)-1H-benzo[f]chromene-2-carbonitrile
C20H13ClN2O Ee = 67% Source of chirality: asymmetric synthesis Absolute configuration: (S) (c 0.48, DMSO)
(S)-3-Amino-1-(3-chlorophenyl)-1H-benzo[f]chromene-2-carbonitrile
C20H13ClN2O Ee = 65% Source of chirality: asymmetric synthesis Absolute configuration: (S) (c 0.62, DMSO)
(S)-3-Amino-1-(furan-2-yl)-1H-benzo[f]chromene-2-carbonitrile
C18H12N2O2 Ee = 61% Source of chirality: asymmetric synthesis Absolute configuration: (S) (c 0.41, DMSO)
(S)-3-Amino-1-pentyl-1H-benzo[f]chromene-2-carbonitrile
C19H20N2O Ee = 57% Source of chirality: asymmetric synthesis Absolute configuration: (S) (c 0.64, CDCl3)
(S)-3-Amino-1-(4-fluorophenyl)-9-methoxy-1H-benzo[f]chromene-2-carbonitrile
C21H15FN2O2 Ee = 66% Source of chirality: asymmetric synthesis Absolute configuration: (S) (c 0.54, DMSO)
(S)-Ethyl 3-amino-1-(4-chlorophenyl)-1H-benzo[f]chromene-2-carboxylate
C22H18ClNO2 Ee = 34% Source of chirality: asymmetric synthesis Absolute configuration: (S) (c 0.33, CDCl3)
| Asymmetric synthesis of homochiral dibenzylbutyrolactone lignans by conjugate addition to a chiral butenolide Tetrahedron: Asymmetry, Volume 1, Issue 12, 1990, Pages 855-856 Andrew Pelter, Robert S. Ward, D. Martin Jones, Peter Maddocks | ||||
Ar1 = 3,4-dimethoxyphenyl,Ar2 = 3,4-methylenedioxyphenyl
D.e. 100% by n.m.r.
Source of chirality: synthesis from (−)-menthol
Absolute configuration 3S,4R,5R,6R (assigned by correlation with, and X-ray analysis of, related thioether adduct)
C31H40O8 Ar1 = 3,4-dimethoxyphenyl,Ar2 = 3,4-methylenedioxyphenyl D.e. 100% by n.m.r. Source of chirality: synthesis from (−)-menthol Absolute configuration 3S,4R,5R,6R (assigned by correlation with, and X-ray analysis of, related thioether adduct)
C37H44SO8 Ar1 = 3,4-dimethoxyphenyl,Ar2 = 3,4-methylenedioxyphenyl D.e. 100% by n.m.r. Source of chirality: synthesis from (−)-menthol Absolute configuration 3S,4R,5R,6R,7S (assigned by correlation with, and X-ray analysis of, stereoisomer)
C37H44SO8 Ar1 = 3,4-dimethoxyphenyl,Ar2 = 3,4-methylenedioxyphenyl D.e. 100% by n.m.r. Source of chirality: synthesis from (−)-menthol Absolute configuration 3S,4R,5R,6R,7R (assigned by X-ray analysis)
| Asymmetric synthesis of β-lactams via amine additions to 5(R)-menthyloxy-2[5H]-furanone. Tetrahedron: Asymmetry, Volume 2, Issue 8, 1991, Pages 775-778 Marcel Lubben, Ben L. Feringa | ||||
C13H17NO3 E.e.= 92% (by 1H NMR) [α]D25= −18.7 (c 3, CHCl3) Source of chirality: asymmetric synthesis from 5(R)-menthyloxy-2[5H]-furanone Absolute configuration: 4R
N-((S)-α-methylbenzyl)-4(R)-dimethoxymethyl-2-azetidinone.
C14H19NO3 D.e.= 92% (by 1H NMR) [α]D25= +26.0 (c 1.9, CHCl3) Source of chirality: asymmetric synthesis from 5(R)-menthyloxy-2[5H]-furanone Absolute configuration: 4R, 2′S
Methyl-3(R)-benzylamino-4,4-dimethoxybutyrate
C14H21NO4 E.e.= 92% (by 1H NMR) [α]43625= −7.2 (c 1.3, CHCl3) Source of chirality: asymmetric synthesis from 5(R)-menthyloxy-2[5H]-furanone Absolute configuration: 3R
Methyl-3(R)-((S)-α-methylbenzylamino)-4,4-dimethoxybutyrate
C15H23NO4 D.e.= 92% (by 1H NMR) [α]43625= −42.0 (c 2.3, CHCl3) Source of chirality: asymmetric synthesis from 5(R)-menthyloxy-2[5H]-furanone Absolute configuration: 3R, 2′S
3-(1-Hydroxyethyl)-6,6-dimethyl-2-methylenebicyclo[3.1.1]heptane
C12H22O ee> 97% [GC, 1H NMR, 13C NMR] [αD20 = 27.64 (c 0.955, MeOH) Source of chirality: myrtenyl bromide, αD20 (neat) −34.4 (> 97% ee) Absolute configuration: 1R,3S,5R,11R
| Enantioselective synthesis of 2,6-diaminopimelic acid derivatives. Part 3 Tetrahedron: Asymmetry, Volume 13, Issue 5, 5 April 2002, Pages 497-502 Francesca Paradisi, Fabio Piccinelli, Gianni Porzi, Sergio Sandri | ||||
C26H32N2O2 [α]D +132.2 (c 0.5, CHCl3) Source of chirality: (S)-phenethylamine Absolute configuration: 1S,4S
(1R,4S)-2,5-Bis-[N-(1′-phenylisopropyl)]-1-benzyl-3,6-dioxo-bicyclo[3,2,2]nonane
C32H36N2O2 [α]D +69 (c 1.37, CHCl3) Source of chirality: (S)-phenethylamine Absolute configuration: 1R,4S
(1R,4S)-2,5-Bis-[N-(1′-phenylisopropyl)]-3,6-dioxo-1-methoxymethyl-bicyclo[3,2,2]nonane
C27H34N2O3 [α]D +165.7 (c 2.47, CHCl3) Source of chirality: (S)-phenethylamine Absolute configuration: 1R,4S
(2S,6R)-2,6-Diamino-2-methoxymethylpimelic acid
C9H18N2O5 [α]D −19.4 (c 0.68, 1N HCl) Source of chirality: (S)-phenethylamine Absolute configuration: 2S,6R
(2R,6R)-2,6-Diamino-2-methylpimelic acid
C8H16N2O4 [α]D −28.2 (c 0.75, 1N HCl) Source of chirality: (S)-phenethylamine Absolute configuration: 2R,6R
(2S,6R)-2,6-Diamino-2-benzylpimelic acid
C14H20N2O4 [α]D −11.7 (c 0.6, 1N HCl) Source of chirality: (S)-phenethylamine Absolute configuration: 2S,6R
(1R,4R,1′S)-2,5-Bis-[N-(1′-phenethyl)]-2,5-diaza-3,6-dioxo-1-methyl-bicyclo[3,2,2]nonane
C24H28N2O2 [α]D −154.5 (c 0.71, CHCl3) Source of chirality: (S)-phenethylamine Absolute configuration: 1R,4R,1′S
(1R,4R,1′S)-2,5-Bis-[N-(1′-phenethyl)]-1-benzyl-2,5-diaza-3,6-dioxo-bicyclo[3,2,2]nonane
C30H32N2O2 [α]D −194.7 (c 0.59, CHCl3) Source of chirality: (S)-phenethylamine Absolute configuration: 1R,4R,1′S
(1R,4R,1′S)-2,5-Bis-[N-(1′-phenethyl)]-2,5-diaza-3,6-dioxo-1-methoxymethyl-bicyclo[3,2,2]nonane
C25H30N2O3 [α]D −191.3 (c 1.15, CHCl3) Source of chirality: (S)-phenethylamine Absolute configuration: 1R,4R,1′S
(1R,4R,1′S)-2,5-Bis-[N-(1′-phenethyl)]-1-allyl-2,5-diaza-3,6-dioxo-bicyclo[3,2,2]nonane
C26H30N2O2 [α]D −182.7 (c 0.71, CHCl3) Source of chirality: (S)-phenethylamine Absolute configuration: 1R,4R,1′S
(1S,4S,1′S)-2,5-Bis-[N-(1′-phenethyl)]-2,5-diaza-3,6-dioxo-1-methyl-bicyclo[3,2,2]nonane
C24H28N2O2 [α]D −39 (c 0.51, CHCl3) Source of chirality: (S)-phenethylamine Absolute configuration: 1S,4S,1′S
(1S,4S)-2,5-Bis-[N-(1′-phenylisopropyl)]-2,5-diaza-3,6-dioxo-bicyclo[3,2,2]nonane
C25H30N2O2 [α]D +166.7 (c 0.66, CHCl3) Source of chirality: (S)-phenethylamine Absolute configuration: 1S,4S
| Asymmetric synthesis of O-benzoyl cyanohydrins by reaction of aldehydes with benzoyl cyanide catalysed by BINOLAM–Ti(IV) complexes Tetrahedron: Asymmetry, Volume 16, Issue 14, 18 July 2005, Pages 2385-2389 Alejandro Baeza, Carmen Nájera, José M. Sansano, José M. Saá | ||||
C15H12NO2 Ee = 68% Source of chirality: (R)-BINOLAM Absolute configuration: (S) (c 2, CHCl3)
(R)-2-(Benzoyloxy)-2-(4-methoxyphenyl)acetonitrile
C16H13NO2 Ee = 56% Source of chirality: (S)-BINOLAM Absolute configuration: (R) (c 1, CHCl3)
(R)-2-(Benzoyloxy)-2-(4-chlorophenyl)acetonitrile
C15H10ClNO4 Ee = 58% Source of chirality: (S)-BINOLAM Absolute configuration: (R) (c 1, CHCl3)
(S)-2-(Benzoyloxy)-2-furylacetonitrile
C13H9NO3 Ee = 55% Source of chirality: (S)-BINOLAM Absolute configuration: (S) (c 1, CHCl3)
(R)-2-(Benzoyloxy)-3-nonenenitrile
C16H19NO2 Ee = 68% Source of chirality: (S)-BINOLAM Absolute configuration: (R) (c 0.5, CHCl3)
(R)-2-(Benzoyloxy)octanenitrile
C15H19NO2 Ee = 58% Source of chirality: (S)-BINOLAM Absolute configuration: (R) (c 0.7, CHCl3)
(R)-2-(Benzoyloxy)-4-phenylbutanenitrile
C17H16NO2 Ee = 65% Source of chirality: (S)-BINOLAM Absolute configuration: (R) (c 2, CHCl3)
| Highly diastereo- and enantioselective catalytic synthesis of the bis-tetrahydrofuran alcohol of Brecanavir and Darunavir Tetrahedron: Asymmetry, Volume 19, Issue 17, 8 September 2008, Pages 2015-2019 David M. Black, Roman Davis, Brian D. Doan, Tom C. Lovelace, Alan Millar, Jennifer F. Toczko, Shiping Xie | ||||
C6H10O3 Er = 97:3 (chiral GC analysis) Source of chirality: asymmetric catalysis with [Cu((S,S)-phenyl-bis(oxazolinyl)pyridine)](SbF6)2 Absolute configuration: (S,S) Absolute configuration: (3S,3aS,6aR) (c 1.40, CHCl3)
(3aR,6aR)-Tetrahydrofuro[2,3-b]furan-3(2H)-one
C6H8O3 Er = 97:3 Source of chirality: asymmetric catalysis with [Cu((S,S)-phenyl-bis(oxazolinyl)pyridine)](SbF6)2 Absolute configuration: (S,S) Absolute configuration: (3aR,6aR) (c 0.89, CHCl3)
(3R,3aS,6aR)-Hexahydrofuro[2,3-b]furan-3-ol
C6H10O3 Er = 97:3 Source of chirality: asymmetric catalysis with [Cu((S,S)-phenyl-bis(oxazolinyl)pyridine)](SbF6)2 Absolute configuration: (S,S) Absolute configuration: (3R,3aS,6aR) (c 0.73, MeOH)
(3S)-3-[(1S)-2-(Benzyloxy)-1-hydroxyethyl]dihydrofuran-2(3H)-one
C13H16O4 Er = 97:3 Source of chirality: asymmetric catalysis with [Cu((S,S)-phenyl-bis(oxazolinyl)pyridine)](SbF6)2 Absolute configuration: (S,S) Absolute configuration: (S,S) (c 2.61, CHCl2)
| Structure requirements for antiproliferative and cytotoxic activities of marine coral prostanoids from the Japanese stolonifer Prostaglandins, Volume 36, Issue 5, November 1988, Pages 621-630 Atsushi Honda, Yo Mori, Kazuo Iguchi, Yasuji Yamada | ||||
| Determination of absolute configuration of axially chiral biaryls Tetrahedron Letters, Volume 22, Issue 7, 1981, Pages 659-662 Kuninobu Kabuto, Fujiko Yasuhara, Shozo Yamaguchi | ||||
| Three new chlorinated marine steroids, yonarasterols G, H and I, isolated from the Okinawan soft coral, Clavularia viridis Steroids, Volume 66, Issue 1, 1 January 2001, Pages 25-32 Makoto Iwashima, Ken Nara, Yoshiyuki Nakamichi, Kazuo Iguchi | ||||
| Clavirins, a new type of marine oxylipins with growth-inhibitory activity from the Okinawan soft coral, Clavularia viridis Tetrahedron Letters, Volume 40, Issue 35, 27 August 1999, Pages 6455-6459 Makoto Iwashima, Katsumi Okamoto, Kazuo Iguchi | ||||
| Enantioselective synthesis of (R)- and (S)-5-dimethylaminomethyl-4,5-dihydro-2(3H)-furanone methobromide - constrained analogues of acetylcholine Tetrahedron: Asymmetry, Volume 3, Issue 12, December 1992, Pages 1537-1538 Jochen Lehmann, Birgit Pieper | ||||
C7H11NO3 [α]D25 = −35.9(c = 1, CH3OH) Source of chirality: D-glutamic acid Absolute configuration: 2R
(S)-(+)-5-dimethylaminomethy]-4,5-dihydro-2(3H)furanone, hydrobromid
C7H14BrNO2 E.e. = > 99% (nmr with (S)-(+)-1-(9-anthryl)-2,2.2-trifluorethanol) [α]D23 =+62.7 (c = 1, CH3OH) Source of chirality: L-glutamic acid Absolute configuration: 5S
(S)-(+)-5-dimethylaminomethyl-4,5-dihydro-2(3Hfuranone, methobromide
C8H16BrNO2 [α]D20 = +49.4(c = 1, CH3OH) Source of chirality: L-glutamic acid Absolute configuration: 5S
| Enantioselective synthesis of (+) and (-)-cis-3-aminocyclo-pentanecarboxylic acids by enzymatic asymmetrization Tetrahedron: Asymmetry, Volume 3, Issue 2, 1992, Pages 199-200 Robert Chênevert, Richard Martin | ||||
C8H12O4 ee = 90% (NMR, derivative with (S)-1-(1-napthyl) ethyl amine [α]D20 = +0.5 (C 3.5, CHCl3) Source of chirality: enzymatic hydrolysis Absolute configuration: 1S, 3R
cis-3-Aminocyclopentanecarboxylic acid
C6H11O2N ee = 90% (NMR, N-trifluoroacetyl derivative with (S)-1-(napthyl) ethyl amine [α]D20 = +6.4 (C 1, H2O) Source of chirality: enzymatic hydrolysis Absolute configuration: 1S, 3R
| Enantioselective synthesis of the AB ring fragment of gambiertoxin 4B. Implication for the absolute configuration of gambiertoxin 4B and ciguatoxin Tetrahedron Letters, Volume 32, Issue 35, 1991, Pages 4505-4508 Toshio Suzuki, Ohki Sato, Masahiro Hirama, Yoshinori Yamamoto, Michio Murata and, Takeshi Yasumoto, Nobuyuki Harada | ||||
| Enantioselective synthesis of 3-hydroxycitronellic acid isolated from Ceratocystis fimbriata sp. platani Tetrahedron: Asymmetry, Volume 7, Issue 7, July 1996, Pages 2023-2028 Abdellatif Fkyerat, Nicolas Burki, Raffaele Tabacchi | ||||
[α]D25=2.3(c 0.51, MeOH)
Source of chirality: asymmetric synthesis.
Absolute configuration: 3R
(R) 3-hydroxy-citronellic acid [α]D25=−1.9(c 0.33, MeOH) [α]D25=−2.0(c 0.02, MeOH) (natural) Source of chirality: natural, asymmetric synthesis. Absolute configuration: 3R
(S) Methyl 3-hydroxy-citronellate [α]D25=+3.8(c 0.17, MeOH) Source of chirality: asymmetric synthesis. Absolute configuration: 3S
| Enantioselective synthesis of (2R,3S)-(+)-catechin Tetrahedron: Asymmetry, Volume 13, Issue 7, 2 May 2002, Pages 715-720 Sang-sup Jew, Doo-yeon Lim, So-young Bae, Hyun-ah Kim, Jeong-hoon Kim, Jihye Lee, Hyeung-geun Park | ||||
C14H20O8 [α]D20=+3.9 (c 1.7, CHCl3) Source of chirality: asymmetric dihydroxylation Absolute configuration: 2R,3S
Methyl (2R,3S)-2,3-methoxymethoxy-3-[3′,4′-bis(methoxymethoxy)phenyl]propionate
C18H28O10 [α]D20=+110.0 (c 0.9, CHCl3) Source of chirality: asymmetric dihydroxylation Absolute configuration: 2R,3S
(2R,3S)-2,3-Methoxymethoxy-3-[3′,4′-bis(methoxymethoxy)phenyl]propionaldehyde
C17H26O10 [α]D20=+131.6 (c 0.95, CHCl3) Source of chirality: asymmetric dihydroxylation Absolute configuration: 2R,3S
(2R,3S)-(+)-Catechin
C17H14O6 [α]D20=+16.0 (c 0.1, CH3COCH3) Source of chirality: asymmetric dihydroxylation Absolute configuration: 2R,3S
| Efficient chemoenzymatic enantioselective synthesis of diacylglycerols (DAG) Tetrahedron: Asymmetry, Volume 15, Issue 18, 20 September 2004, Pages 2889-2892 Giuseppe Guanti, Luca Banfi, Andrea Basso, Elisabetta Bevilacqua, Laura Bondanza, Renata Riva | ||||
C10H14O3 Ee = 96.0% [by NMR or HPLC of Mosher’s double ester] Source of chirality: enzymatic double kinetic resolution/Mitsunobu inversion Absolute configuration; R (assigned by chemical correlation) (c 20, CHCl3)
| Enantioselective synthesis of cinnamyl-1-phenyl-2-propenyl ether: A metabolite of marine green algal species caulerpa racemosa Tetrahedron: Asymmetry, Volume 5, Issue 1, January 1994, Pages 23-26 U. V. Mallavadhani, Y. R. Rao | ||||
C9H10O e.e.: 88% (by 1HNMR of the MTPA ester) [α]D28 = +2.4 (c, 2.1; CHCl3) Source of chirality: lipase catalysed kinetic resolution. Absolute configuration: R.
S-(−)-cinnamyl-1-phenyl-2-propenylether
C18H18O [α]D28: −4.5 (c, 2.1; CHCl3) Source of chirality: lipase catalysed kinetic resolution of intermediate carbinol. Absolute configuration: S.
| Efficient enantioselective synthesis of (+)-sclareolide and (+)-tetrahydroactinidiolide: chiral LBA-induced biomimetic cyclization Tetrahedron: Asymmetry, Volume 20, Issue 14, 29 July 2009, Pages 1637-1640 Kiran B. Upar, Sanjay J. Mishra, Shrikant P. Nalawade, Soni A. Singh, Reena P. Khandare, Sujata V. Bhat | ||||
C16H26O2 Ee = 87.9% Source of chirality: asymmetric synthesis Absolute configuration: (3aR,5aS,9aS,9bR) (c 0.5 CHCl3)
(3aR,7aS)-Octahydro-4,4,7a-trimethyl-benzofuran-2-one
C11H18O2 Ee = 89.9% Source of chirality: asymmetric synthesis Absolute configuration: (3aR,7aR) (c 1, hexane)
| Improved Schöllkopf construction of quaternary α-amino acids: efficient enantioselective synthesis of integrin LFA-1 antagonist BIRT-377 Tetrahedron: Asymmetry, Volume 17, Issue 11, 17 July 2006, Pages 1754-1757 Stamatia Vassiliou, Plato A. Magriotis | ||||
C17H22BrN2O2 Ee = 100% Source of chirality: asymmetric synthesis Absolute configuration: (3R,6S) (c 1, CH2Cl2)
Methyl (2R)-2-amino-3-(4-bromophenyl)-2-methylpropanoate
C11H14BrNO2 Ee = >99% Source of chirality: asymmetric synthesis Absolute configuration: 2R (c 1, CH2Cl2)
(5R)-5-(4-Bromobenzyl)-3-(3,5-dichlorophenyl)-5-methyl-1H-imidazole-2,4(3H,5H)-dione
C17H13BrCl2N2O2 Ee = >99% Source of chirality: asymmetric synthesis Absolute configuration: 5R (c 1, CH2Cl2)
(5R)-5-(4-Bromobenzyl)-3-(3,5-dichlorophenyl)-1,5-dimethyl-1H-imidazole-2,4(3H,5H)-dione
C18H15BrCl2N2O2 Ee = >99% Source of chirality: asymmetric synthesis Absolute configuration: 5R (c 1, EtOH)
| The first total synthesis of (R)-7-butyl-6,8-dihydroxy-3-pentylisochroman-1-one Tetrahedron: Asymmetry, Volume 16, Issue 13, 4 July 2005, Pages 2231-2234 Weiguo Quan, Junying Ma, Xuanjia Peng, Tongxing Wu, Xuegong She, Xinfu Pan | ||||
C19H32O4 Ee 95% Source of chirality: enantioselective synthesis Absolute configuration: 1R,2R (c 1.0, CH3OH)
(R)-1-(4-Butyl-3,5-dimethoxyphenyl)heptan-2-ol
C19H32O3 Ee 93% Source of chirality: enantioselective synthesis Absolute configuration: R (c 1.0, CH3OH)
2-Butyl-1,3-dimethoxy-5-((R)-2-methoxyheptyl)benzene
C20H34O3 Ee 93% Source of chirality: enantioselective synthesis Absolute configuration: R (c 1.0, CH3OH)
2-Bromo-4-butyl-3,5-dimethoxy-1-((R)-2-methoxyheptyl)benzene
C20H33BrO3 Ee 93% Source of chirality: enantioselective synthesis Absolute configuration: R (c 1.0, CH3OH)
Ethyl 3-butyl-2,4-dimethoxy-6-((R)-2-methoxyheptyl)benzoate
C23H38O5 Ee 93% Source of chirality: enantioselective synthesis Absolute configuration: R (c 1.02, CH3OH)
7-Butyl-6,8-dihydroxy-3(R)-pentylisochroman-1-one
C18H26O4 Ee 93% Source of chirality: enantioselective synthesis Absolute configuration: R (c 0.1, CH3OH)
| Asymmetric synthesis of unsaturated α-benzyloxyaldehydes: an enantioselective synthesis of (+)-exo-brevicomin Tetrahedron: Asymmetry, Volume 16, Issue 24, 12 December 2005, Pages 3951-3953 Kavirayani R. Prasad, Pazhamalai Anbarasan | ||||
■ [α]D = +10.5 (c 1.8, CHCl3) Source of chirality: Absolute configuration: (4S,5S)
(+)-(4S,5S)-4,5-Bis(1-oxohex-5-enyl)-2,2-dimethyl-1,3-dioxolane
■ [α]D = +11.6 (c 1.2, CHCl3) Source of chirality: Absolute configuration: (4S,5S)
(−)-(4S,5S)-4,5-Bis[(R)-1-(hydroxy)pent-4-enyl]-2,2-dimethyl-1,3-dioxolane
■ [α]D = −7.8 (c 2.8, CHCl3) Source of chirality: Absolute configuration: (4S,5S)
(−)-(4S,5S)-4,5-Bis[(R)-1-(hydroxy)hex-5-enyl]-2,2-dimethyl-1,3-dioxolane
■ [α]D = −7.5 (c 1.1, CHCl3) Source of chirality: Absolute configuration: (4S,5S)
(−)-(5R,6R,7R,8R)-5,8-Bis(benzyloxy)dodeca-1,11-diene-6,7-diol
■ [α]D = −24.4 (c 1.8, CHCl3) Source of chirality: Absolute configuration: (5R,6R,7R,8R)
(−)-(6R,7R,8R,9R)-6,9-Bis(benzyloxy)tetradeca-1,13-diene-7,8-diol
■ [α]D = −25.8 (c 2.1, CHCl3) Source of chirality: Absolute configuration: (6R,7R,8R,9R)
(+)-(R)-2-(Benzyloxy)hept-6-enal
■ [α]D = +20.5 (c 1.4, CHCl3) Source of chirality: Absolute configuration: (2R)
(+)-exo-Brevicomin
■ [α]D = +66.6 (c 0.3, Et2O) Source of chirality:
| Remote asymmetric induction. Stereo- and enantioselective synthesis of symmetrical and unsymmetrical 1,4-diols. Tetrahedron: Asymmetry, Volume 3, Issue 3, 1992, Pages 333-336 Robert Bloch, Cécile Brillet | ||||
C10H16O3 [α]20D = −42 (c 1, CHCl3) Source of chirality: from a precursor obtained by enzymatic hydrolysis Absolute configuration:1R,2R,3S,4S,1′R,1″R
2-(1′-Hydroxypentyl)-3-(1″-hydroxyethyl)-7-oxabicyclo[2.2.1]hept-5-ene
C14H24O3 [α]20D =12 (c0.8, CHCl3) Source of chirality: from a precursor obtained by enzymatic hydrolysis Absolute configuration:1R,2R,3S,4S,1′R,1″S
3-Hexen-2,5-diol
C6H12O2 E.e> 95% [α]20D = −62 (c 1, CHCl3) Source of chirality: from a precursor obtained by enzymatic hydrolysis Absolute configuration: 2R,5R
4-Decen-3,6-diol
C10H20O2 E.e> 95% (1H NMR with Eu(hfc)3) [α]20D = 14 (c 0.8, CHCl3) Source of chirality: from a precursor obtained by enzymatic hydrolysis Absolute configuration: 3S,6R
| Enantioselective synthesis of 2-substituted-N-Boc-Δ-4,5-piperidines Tetrahedron: Asymmetry, Volume 11, Issue 23, 1 December 2000, Pages 4639-4643 Claude Agami, François Couty, Gwilherm Evano | ||||
C16H21NO2 Ee=87% [α]D20=−39 (c 1.5, CHCl3) Source of chirality: asymmetric synthesis Absolute configuration: (2S)
(2S)-2-Propyl-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester
C13H23NO2 Ee=80% [α]D20=+30.8 (c 1.75, CHCl3) Source of chirality: asymmetric synthesis Absolute configuration: (2R)
(E,2S)-2-Oct-1-enyl-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester
C18H31NO2 Ee >95% [α]D20=−25 (c 1.1, CHCl3) Source of chirality: asymmetric synthesis Absolute configuration: (2S)
| Stereocontrolled Preparation of Stereocomplementary Regioisomeric Tricarbonyliron Complexes in Enantiopure Form Tetrahedron, Volume 56, Issue 15, 7 April 2000, Pages 2273-2281 Christopher E. Anson, Gaurang Dave, G. Richard Stephenson | ||||
| Absolute stereochemistry of the triol moiety of gymnoprenols Tetrahedron Letters, Volume 25, Issue 13, 1984, Pages 1371-1372 Shigeo Nozoe, Yutaka Koike, Genjiro Kusano | ||||
| Enantioselective synthesis of N-Boc-1-naphthylglycine Tetrahedron: Asymmetry, Volume 8, Issue 10, 22 May 1997, Pages 1581-1586 Eva Medina, Anton Vidal-Ferran, Albert Moyano, Miquel A. Pericàs, Antoni Riera | ||||
C13H12O2 E.e. = 86% [α] Source of chirality: Sharpless asym. epoxidation Absolute configuration: 2S, 3S = 50.3 (c=1, CHCl3)
(2R, 3R)-3-diphenylmethylamino-3(1-naphthyl)-1,2-propanediol
C26H25NO2 E.e. = 85% [α] mp = 55–57 °C Source of chirality: Sharpless asym. epoxidation Absolute configuration: 2R, 3R = 11.2 (c=1, CHCl3)
(2R, 3R)-3-ter-butoxycarbonylamino-3-(1-naphthyl)-1,2-propanediol
C18H23O4N E.e. = > 99% [α] mp = 108–109 °C Source of chirality: Sharpless asym. epoxidation Absolute configuration: 2R, 3R = −16.0 (c=1, CHCl3)
N-Boc-D-1-naphthylglycine
C17H19O4N E.e. = > 99% [α] mp = 182–183 °C Source of chirality: Sharpless asym. epoxidation Absolute configuration: R = −147.7 (c=1, MeOH)
N-Boc-D-1-naphthylglycine methly ester
C18H21O4N E.e. = > 99% [α] Source of chirality: Sharpless asym. epoxidation Absolute configuration: R = −144 (c=1, CHCl3)
| Use of a selone chiral derivatizing agent for the absolute configurational assignment of stereogenic centers. Tetrahedron: Asymmetry, Volume 5, Issue 9, September 1994, Pages 1627-1630 Jie Peng, Jerome D. Odom, R. Bruce Dunlap, Louis A. SilksIII | ||||
Absolute configuration of parent amino acids can be assessed using 77Se NMR, TLC, UV, and CD.
R= CH3-, (CH3)2CH-, (CH3)2CHCH2-,CH3CH2(CH3)CH-, CH3S(CH2)2-, C6H5CH2-, CH2CH2CH2-
Absolute configuration of parent amino acids can be assessed using 77Se NMR, TLC, UV, and CD. R= CH3-, (CH3)2CH-, (CH3)2CHCH2-,CH3CH2(CH3)CH-, CH3S(CH2)2-, C6H5CH2-, and CH2CH2CH2-.
| Enantioselective synthesis and absolute configurations of aculeatins A and B Tetrahedron Letters, Volume 46, Issue 48, 28 November 2005, Pages 8407-8410 Eva Falomir, Paula Álvarez-Bercedo, Miguel Carda, J. Alberto Marco | ||||
| First enantioselective synthesis of the antitumour alkaloid (+)-crispine A and determination of its enantiomeric purity by 1H NMR Tetrahedron: Asymmetry, Volume 16, Issue 22, 14 November 2005, Pages 3619-3621 Joanna Szawkało, Anna Zawadzka, Krystyna Wojtasiewicz, Andrzej Leniewski, Józef Drabowicz, Zbigniew Czarnocki | ||||
C14H19NO2 Source of chirality: asymmetric transfer hydrogenation Absolute configuration: (R) (c 1, CHCl3)
| Enantioselective synthesis of (+)-α-vetivone through the Michael reaction of chiral imines Tetrahedron: Asymmetry, Volume 11, Issue 24, 15 December 2000, Pages 4975-4983 Gilbert Revial, Ivan Jabin, Michel Pfau | ||||
C14H21NO Ee=100% [α]D20=−212 (c 0.9, EtOH) Source of chirality: asymmetric synthesis Absolute configuration: (4R,4aS)
(3R,1S)-(−)-3-(5-Isopropylidene-1-methyl-2-oxo-cyclohexyl)butyric acid
C14H22O3 Ee=100% [α]D20=−49.5 (c 1.4, EtOH) Source of chirality: asymmetric synthesis Absolute configuration: (3R,1S)
(4R,4aR)-(−)-4,4a-Dimethyl-6-isopropylidene-3,4,4a,5,6,7-hexahydrochromen-2-one
C14H20O2 Ee=100% [α]D20=−137 (c 2.8, EtOH) Source of chirality: asymmetric synthesis Absolute configuration: (4R,4aS)
(4R,4aR)-(+)-4,4a-Dimethyl-6-isopropylidene-4,4a,5,6,7,8-hexahydro-(3H)-naphthalen-2-one, (+)-α-vetivone
C15H22O Ee=100% [α]D20=+219 (c 0.5, EtOH) Source of chirality: asymmetric synthesis Absolute configuration: (4R,4aS)
| An efficient, enantioselective synthesis of branched polyhydroxylated pyrrolidines Tetrahedron Letters, Volume 41, Issue 49, 2 December 2000, Pages 9377-9381 Mark F. Mechelke, A. I. Meyers | ||||
| Enantioselective synthesis of 2-fluoro carboxylic acids from Trichloromethyl carbinols: an efficient approach to chiral fluorine introduction into insect sex pheromones Tetrahedron: Asymmetry, Volume 7, Issue 1, 1996, Pages 37-40 Achot P. Khrimian, James E. Oliver, Rolland M. Waters, Sini Panicker, Jesse M. Nicholson, Jerome A. Klun | ||||
C14H25FO2 E.e. = 94 % [GC of (S)-α-methylbenzylamide] [α]D25 = −6.5 (c 0.56 CHCl3) Source of chirality: asymmetric synthesis Absolute configuration S (assigned by correlation with homologous acid)
2-Fluoro-(Z)-9-tetradecenoic acid
C14H25FO2 E.e. = 94 % [GC of (S)-α-methylbenzylamide] [α]D25 = −6.6 (c 1.15 CHCl3) Source of chirality: asymmetric synthesis Absolute configuration S (assigned by correlation with homologous acid)
2-Fluoro-(Z)-11-tetradecen-1-ol acetate
C16H29FO2 E.e. = 92 % (GC Mosher ester of interm.alkyne) [α]D25 = −4.6 (c 0.94 CHCl3) Source of chirality: 2-fluoro carboxylic acid Absolute configuration R (assigned by chemical correlation)
2-Fluoro-(Z)-9-tetrahedron-1-ol acetate
C16H29FO2 E.e. = 92 % (GC Mosher ester of interm.alkyne) [α]D25 = +4.4 (c 1.01 CHCl3) Source of chirality: 2-fluoro carboxylic acid Absolute configuration S (assigned by chemical correlation)
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