ࡱ5. for C15H28O2Si (268.47): C 67.11, H 10.51. Found: C 67.16, H 10.69. 3-(Dimethylphenylsilyl)-2,4-dimethoxy-3-methyl-1,4-cyclohexadiene (7) 1,5-Dimethoxy-1,4-cyclohexadiene (280 mg, 2 mmol) was dissolved in THF (7 mL). The soln. was cooled to ca. 70 C. After addition of tert-butyllithium (1.4 mL, 1.6 M in hexane, 2.2 mmol) and stirring for 30 min, HMPA (0.42 mL, 2.4 mmol) was added. The resulting red soln. was stirred for 10 min at 70 C. A soln. of DMPSCl (0.37 mL, 2.2 mmol) in THF (2 mL) was slowly added. The red color of the reaction mixture disappeared. After stirring for 1 h at 70 C, butyllithium (1.6 mL, 1.5 M in hexane, 2.4 mmol) was added. The mixture turned orange. After stirring for 1 h at 70 C, (CH3O)2SO2 (0.2 mL, 2.1 mmol) was added. The color of the reaction mixture disappeared. After 5 min, the cooling bath was removed and the reaction mixture was allowed to warm to room temperature. After addition of pentane and H2O, the phases were separated. The organic layer was washed with H2O and brine. The soln. was dried over MgSO4 and concentrated in vacuo. Purification by FC (Et2O/pentane = 1 : 20) afforded 7 (427 mg, 74%) as a colorless oil. IR (CHCl3): 3068w, 2998m, 2952m, 2903m, 2831m, 1677s, 1643w, 1451m, 1427m, 1346m, 1127s, 1076w, 979w cm-1. 1H-NMR (400 MHz, CDCl3): ane) afforded 8 (1.46 g, 47 mmol, 38%) as a colorless amorphous solid. I.R. (CHCl3): 2947s, 2866s, 2831s, 1681s, 1642m, 1581w, 1465s, 1343m, 1128s, 980m, 882m cm-1. 1H-NMR (400 MHz, CDCl3): N; over MgSO4 and concentrated in vacuo. After purification by FC (pentane / MTBE 2 : 1), the obtained N-allyl toluenesulfonamide was dissolved in ethanol (5 mL). To the soln., powdered KOH (0.56 g, 10 mmol) was added. Allyl bromide (1.18 mL, 14 mmol) was added dropwise. The mixture was refluxed for 1 h. The same amount of allyl bromide was added and the mixture was refluxed for 2 h. The organic phase was separated from KOH and concentrated in vacuo. Purification by FC (pentane / MTBE 3 : 1) afforded 16 (1.86 g, 7.4 mmol, 74% over two steps) as a colorless oil. The spectroscopic data are in agreement with those reported in the literature.5 4,4-Bis(hydroxymethyl)-1,6-heptadiene (17) was prepared according to a literature procedure.6 5,5-Diallyl-2,2-dimethyl-1,3-dioxane (18) 4,4-Bis(hydroxymethyl)-1,6-heptadiene 17 (625 mg, 4 mmol) and triethyl orthoformiate (1.64 mL, 16 mmol) were dissolved in acetone (4 mL). A catalytic amount of conc. sulfuric acid was added. After refluxing for 4 h, the mixture was washed with sat. NaHCO3 and brine. The organic phase was separated, dried over MgSO4 and concentrated in vacuo. Purification by FC (pentane / MTBE 20 : 1) afforded 18 as a yellowish oil (606 mg, 77%). I.R. (nujol): 3076m, 2993s, 2939m, 2916m, 2860s, 1638m, 1266m, 1232m, 1199s, 1155m, 1104s, 1036m, 916m, 830m cm-1. 1H-NMR (300 MHz, CDCl3): 5MHz, CDCl3): cis-19: 3-[(tert-Butyldimethylsilyl)methyl]-4-methyl-N-(4-Toluenesulfonyl)-pyrrolidine (21) In a sealed tube, N,N-diallyl toluenesulfonamide 16 (251 mg, 1 mmol), 3-tert-butyldimethylsilyl-2,4-dimethoxy-3-methyl-1,4-cyclohexadiene 6 (400 mg, 1.5 mmol) and AIBN (50 mg, 0.3 mmol) were dissolved in hexane (4 mL) and stirred for 7 h at 90 C. Removal of the solvent in vacuo and purification by FC (pentane/ MTBE 10 : 1) afforded 21 (280 mg, 76 %) as a colorless solid. The diastereoisomeric ratio was determined by GC on the crude reaction mixture: dr (cis : trans) 2.0 : 1. M.p. 52 53 C. I.R. (KBr): 2954s, 2926s, 2881s, 2854s, 1922w, 1657w, 1598w, 1464m, 1341s, 1248m, 1157s, 828s, 812s, 672s, 589s, 548s cm-1. 1H-NMR (400 MHz, CDCl3): cis-21: Hz, J2 = 5.1 Hz, Si(CH2)); 0.24 (d(d, 1 H, J1 = 14.8 Hz, J2 = 9.2 Hz, Si(CH2)); 0.11 (2(s, 6 H, Si(CH3)). trans-21: the solvent in vacuo and purification by FC (pentane/ MTBE 30 : 1) afforded 23 (113 mg, 72 %) as a colorless oil. The diastereoisomeric ratio was determined by GC on the crude reaction mixture: dr (cis : trans) 2.6 : 1. I.R. (nujol): 2992s, 2953s, 2855s, 1471s, 1464s, 1381s, 1368s, 1249s, 1209s, 1195s, 1157m, 1080s, 1032m, 831s, 574m cm-1. 1H-NMR (400 MHz, CDCl3): cis-23: 1.88 (d(d, 1 H, J1 = 13.2 Hz, J2 = 9.8 Hz, CCH2); 0.85 (s, 9 H, C(CH3)3); 0.81 (d, 3 H, J = 6.6 Hz, CHCH3); 0.61 (d(d, 1 H, J1 = 14.6 Hz, J2 = 4.6 Hz, Si(CH2)); 0.41 (d(d, 1 H, J1 = 14.6 Hz, J2 = 9.0 Hz, Si(CH2)); 0.04 (2(s, 6 H, Si(CH3)2). 13C-NMR (75 MHz, CDCl3): 198 mg, 0.57 mmol, 57 %) as a colorless oil. The diastereoisomeric ratio was determined by GC on the crude reaction mixture: dr (cis : trans) 4.4 : 1. The NMR-data for the trans-isomer are in agreement with those reported in the literature.8 I.R. (nujol): 2954s, 1734s, 1432m, 1251s, 1200m, 1151m, 1113m, 836m, 730m, 701m cm-1. 1H-NMR (300 MHz, CDCl3): cis-26: .(100); 127.1 (25); 125.1 (24); 122.1 (52); 121.2 (40); 107.1 (23); 81.1 (29); 79.1 (24); 55.1 (31); 29.1 (53); 28.0 (37). Diethyl 4-[(tert-butyldimethylsilyl)methyl]-3-ethyl-cyclohexane-1,1-dicarboxylate (30) In a sealed tube, diethyl 1,7-nonadiene-5,5-dicarboxylate 29 (110 mg, 1 mmol), 3-tert-butyldimethylsilyl-2,4-dimethoxy-3-methyl-1,4-cyclohe-xadiene 6 (400 mg, 1.5 mmol) and AIBN (50 mg, 0.3 mmol) were dissolved in hexane (4 mL) and stirred at 90 C. After 4 h, AIBN (50 mg, 0.3 mmol) was added. After 4 h, removal of the solvent in vacuo and purification by FC (pentane/MTBE 50 : 1) afforded 30 (233 mg, ca. 95 % pure, 0.58 mmol, 61 %) as a colorless oil. The diastereoisomers could not be separated completely by GC: dr (cis : trans) ( 1 : 1. 1H-NMR (400 MHz, CDCl3): cis- and trans-30: iterature.12 Dimethyl 3-hydroxymethyl-4-methyl-cyclopentane-1,1-dicarboxylate (35) Acetic anhydride (5.4 mL, 57 mmol) was treated with 3 drops of conc. sulfuric acid and cooled to 0 C. To this solution, hydrogen peroxide (3.60 mL, 35% in water, 42 mmol) was added. The resulting solution was stirred at room temperature for 30 min. In 6 mL of this solution, dimethyl 3-[(dimethylphenylsilyl)methyl]-4-methyl-cyclopentane-1,1-dicarboxylate 26 (171 mg, 0.49 mmol) was dissolved and treated with Hg(OAc)2 (263 mg, 0.79 mmol).13 The solution was stirred for 5 h at room temperature. Diethyl ether (80 mL) was added. The organic phase was separated and consecutively washed with sat. Na2S2O3-soln., H2O, NaHCO3-soln. and brine. The organic phase was dried over MgSO4. Filtration and removal of the solvent in vacuo yielded the crude product which was purified by FC (pentane/ MTBE 1 : 1) to afford 35 (83 mg, 0.36 mmol, 74 %) as a colorless oil. The diastereoisomeric ratio was determined with GC on the crude reaction mixture: dr (cis : trans) 4 : 1. The NMR-data for the trans-isomer are in agreement with those reported in the literature.8 cis-35: 1H-NMR (300 MHz, CDCl3): lsi, M. Tetrahedron: Asymmetry 1999, 10, 2775. Zhang, S.-W.; Mitsudo, T.; Kondo, T.; Watanabe, Y. J. Organomet. Chem. 1993, 450, 197. Widenhoefer, R. A.; Stengone, C. N. J. Org. Chem. 1999, 64, 8681. Miura, K.; Oshima, K.; Utimoto, K. Bull. Chem. Soc. Jpn. 1993, 66, 2348. 10. Eccott, E. N.; Linstead, R. P. J. Chem. Soc. 1929, 2153. The spectroscopic data are in agreement with those reported in the literature: Takeuchi, R.; Kashio, M. J. Am. Chem. Soc. 1998, 120, 8647. 11. Bhatarah, P.; Smith, E. H. J. Chem. Soc., Perkin Trans. 1 1990, 2603. 12. Ojima, I.; Zhu, J.; Vidal, E. S.; Kass, D. F. J. Am. Chem. Soc. 1998, 120, 6690. 13. Fleming, I.; Sanderson, P. E. J. Tetrahedron Lett. 1987, 28, 4229. 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