Table of Contents

May 2003
Volume 7, Issue 3
Pages 225-448

Editorial

Dangers of the Unknown

Trevor Laird
p 225
Publication Date (Web): April 26, 2003 (Editorial)
DOI: 10.1021/op034047r

Highlights from the Literature

Some Items of Interest to Process R&D Chemists and Engineers

Trevor Laird*Stephen A. HermitageUlf Tilstam
pp 226–236
Publication Date (Web): May 16, 2003 (Editorial)
DOI: 10.1021/op034046z

Articles

Thorough Examination of a Wittig−Horner Reaction Using Reaction Calorimetry (RC-1), LabMax, and ReactIR

Michael Grabarnick and Sharona Zamir*
pp 237–243
Publication Date (Web): March 19, 2003 (Article)
DOI: 10.1021/op020075i

The Chemical Development and Scale-Up of Sampatrilat1

Peter J. Dunn,* Michael L. Hughes, Patricia M. Searle, and Albert S. Wood
pp 244–253
Publication Date (Web): March 22, 2003 (Article)
DOI: 10.1021/op020091f

Environmentally Friendly Solvent-Free Processes:  Novel Dual Catalyst System in Henry Reaction

Apurba Bhattacharya* and Vikram C. PurohitFrank Rinaldi
pp 254–258
Publication Date (Web): March 01, 2003 (Article)
DOI: 10.1021/op020222c

Antisense Phosphorothioate Oligodeoxyribonucleotide Targeted against ICAM-1:  Use of I-Linker to Eliminate 3‘-Terminal Phosphorothioate Monoester Formation

Vasulinga T. Ravikumar,* R. Krishna Kumar, Daniel C. Capaldi, Brett Turney, Claus Rentel, and Douglas L. Cole
pp 259–266
Publication Date (Web): March 21, 2003 (Article)
DOI: 10.1021/op020098x

Process Optimization and Synthesis of 3-(4-Fluorophenyl)-4,5-dihydro-N-[4-(tri- fluoromethyl)phenyl]-4-[5-(trifluoromethyl)-2-pyridyl]-1H-pyrazole-1-carboxamide

James M. Renga,* Kevin L. McLaren, and Michael J. Ricks
pp 267–271
Publication Date (Web): April 02, 2003 (Article)
DOI: 10.1021/op025619v

Process Development Implications of Biotin Production Scale-Up

Aleksander Warm,* Andrew B. Naughton, and Elie A. Saikali
pp 272–284
Publication Date (Web): April 15, 2003 (Article)
DOI: 10.1021/op020089o

A Scalable Asymmetric Synthesis of (R)-2-Amino-1-(3-pyridinyl)ethanol Dihydrochloride via an Oxazaborolidine Catalyzed Borane Reduction

Jason Duquette,* Mingbao Zhang, Lei Zhu, and Raymond S. Reeves
pp 285–288
Publication Date (Web): April 15, 2003 (Article)
DOI: 10.1021/op0340208

Lecture Transcripts

There's No Industrial Biocatalyst Like Hydrolase:  Development of Scalable Enantioselective Processes Using Hydrolytic Enzymes1

Yasuo Chikusa, Yoshihiro Hirayama, Masaya Ikunaka,* Toru Inoue, Shunji Kamiyama, Masafumi Moriwaki, Yukifumi Nishimoto, Fumiki Nomoto, Kazuo Ogawa, Tomoyasu Ohno,§ Koutaro Otsuka, Akiko K. Sakota, Naoki Shirasaka, Atsuko Uzura, and Kensaku Uzura
pp 289–296
Publication Date (Web): April 09, 2003 (Summary of Lecture Transcript)
DOI: 10.1021/op034014b

Scale-Up of Polymerization Process:  A Practical Example

Thierry Meyer*
pp 297–302
Publication Date (Web): March 12, 2003 (Summary of Lecture Transcript)
DOI: 10.1021/op025605p

Technical Notes

One-Step Preparation of Some 3-Substituted Anisoles

Joseph Zilberman*
pp 303–305
Publication Date (Web): March 08, 2003 (Technical Note)
DOI: 10.1021/op020058t

A One-Pot Efficient Process for 16-Dehydropregnenolone Acetate

Amrit Goswami,* Rumi Kotoky, Romesh C. Rastogi, and Anil C. Ghosh
pp 306–308
Publication Date (Web): February 14, 2003 (Technical Note)
DOI: 10.1021/op0200625

A New Route to Prepare 6-Chloro-5-(2-chloroethyl)oxindole

Mukund K. Gurjar,* A. M. S. Murugaiah, and Dandepally Srinivasa ReddyMukund S. Chorghade
pp 309–312
Publication Date (Web): February 20, 2003 (Technical Note)
DOI: 10.1021/op020095k

Rapid Improvement of a Reductive Sulfonylation Using Design of Experiment Methods

Jiong Jack Chen,*§ Thomas C. Nugent,* Cuong V. Lu,§ Sudharani Kondapally, Peter Giannousis, Ying Wang,§ and Jeremy T. Wilmot§
pp 313–317
Publication Date (Web): March 28, 2003 (Technical Note)
DOI: 10.1021/op034018g

The Nitration of 8-Methylquinoxalines in Mixed Acid

Wolfgang Marterer,* Walter Prikoszovich, Jacques Wiss, and Mahavir Prashad
pp 318–323
Publication Date (Web): April 04, 2003 (Technical Note)
DOI: 10.1021/op0340255

Technology Reports

In Situ Recycling of Chiral Ligand and Surplus Nucleophile for a Noncatalytic Reaction:  Amplification of Process Throughput in the Asymmetric Addition Step of Efavirenz (DMP 266)

Anusuya Choudhury,* James R. Moore, Michael E. Pierce, Joseph M. Fortunak, Ioannis Valvis, and Pat N. Confalone
pp 324–328
Publication Date (Web): March 14, 2003 (Technology Report)
DOI: 10.1021/op025595s

Reinvestigation of the Reaction of Trichloroacetyl Chloride and Acrylonitrile in the Preparation of 3,5,6-Trichloropyridin-2-ol

H. Fakhraian,* A. Moghimi, A. Bazaz, H. Hadj-Ghanbary, and M. Sadeghi
pp 329–333
Publication Date (Web): April 03, 2003 (Technology Report)
DOI: 10.1021/op025610t

Control of Crystal Habit and Size of Cefmatilen Hydrochloride Hydrate with a Habit Modifier

Yoshiyuki Masui,* Yoji Kitaura, Tatsuya Kobayashi, Yoshihisa Goto, Satoru Ando, Akira Okuyama, and Hisanori Takahashi
pp 334–338
Publication Date (Web): March 26, 2003 (Technology Report)
DOI: 10.1021/op0256082

Safety and Environmental Reports

Functional Group Transformations of Diols, Cyclic Ethers, and Lactones Using Aqueous Hydrobromic Acid and Phase Transfer Catalyst under Microwave Irradiation

Goverdhan L. Kad,* Irvinder Kaur, Monica Bhandari, Jasvinder Singh, and Jasamrit Kaur
pp 339–340
Publication Date (Web): April 03, 2003 (Safety/Environmental Report)
DOI: 10.1021/op025606h

Special Feature Section: Homogeneous Transition Metal-Catalyzed Reactions

SPECIAL FEATURE SECTION: HOMOGENEOUS TRANSITION METAL-CATALYZED REACTIONS

Ian C. Lennon*Christian T. Goralski
p 341
Publication Date (Web): April 05, 2003 (Editorial)
DOI: 10.1021/op034040+

Platinum Group Metals in Catalysis:  Fabrication of Catalysts and Catalyst Precursors

Peter B. Kettler*
pp 342–354
Publication Date (Web): March 29, 2003 (Review)
DOI: 10.1021/op034017o

Chiral β-Amino Acid Derivatives via Asymmetric Hydrogenation

Hans-Joachim Drexler, Jingsong You, Songlin Zhang, Christine Fischer, Wolfgang Baumann, Anke Spannenberg, and Detlef Heller*
pp 355–361
Publication Date (Web): April 03, 2003 (Review)
DOI: 10.1021/op034011z

Asymmetric Synthesis of an MMP-3 Inhibitor Incorporating a 2-Alkyl Succinate Motif

Christopher P. Ashcroft, Stephen Challenger, Andrew M. Derrick, Richard Storey, and Nicholas M. Thomson*
pp 362–368
Publication Date (Web): March 22, 2003 (Article)
DOI: 10.1021/op034001y

The Synthesis of the High-Potency Sweetener, NC-00637. Part 1:  The Synthesis of (S)-2-Methylhexanoic Acid

David J. Ager,* Scott Babler, Diane E. Froen, Scott A. Laneman, David P. Pantaleone, Indra Prakash, and Ben Zhi
pp 369–378
Publication Date (Web): April 18, 2003 (Technology Report)
DOI: 10.1021/op025616i

Practical Preparation and Resolution of 1-(2‘-Diphenylphosphino-1‘-naphthyl)isoquinoline:  A Useful Ligand for Catalytic Asymmetric Synthesis

Chung Woo Lim, Olivier Tissot, Andrew Mattison, Mark W. Hooper, John M. Brown,* Andrew R. Cowley, David I. Hulmes,§ and A. John Blacker§
pp 379–384
Publication Date (Web): May 16, 2003 (Article)
DOI: 10.1021/op034007n

The Synthesis of OSU 6162:  Efficient, Large-Scale Implementation of a Suzuki Coupling

Michael F. Lipton,* Michael A. Mauragis, Mark T. Maloney, Michael F. Veley, Dale W. VanderBor, John J. Newby, Robert B. Appell, and Edward D. Daugs
pp 385–392
Publication Date (Web): February 08, 2003 (Article)
DOI: 10.1021/op025620u

Application of Immobilized Rhodium Catalyst Precursors in Enantio- and Chemoselective Hydrogenation Reactions

Jim A. M. Brandts* and Peter H. Berben
pp 393–398
Publication Date (Web): April 15, 2003 (Article)
DOI: 10.1021/op034004a

SYNPHOS: a New Atropisomeric Diphosphine Ligand. From Laboratory-scale Synthesis to Scale-up Development

Sébastien Duprat de Paule, Séverine Jeulin, Virginie Ratovelomanana-Vidal, Jean-Pierre Genêt,* Nicolas Champion,* Gilles Deschaux, and Philippe Dellis
pp 399–406
Publication Date (Web): April 16, 2003 (Article)
DOI: 10.1021/op034016w

Highly Efficient Asymmetric Hydrogenation of 2-Methylenesuccinamic Acid Using a Rh-DuPHOS Catalyst

Christopher J. Cobley,* Ian C. Lennon, Céline Praquin, and Antonio Zanotti-GerosaRobert B. Appell, Christian T. Goralski, and Angela C. Sutterer
pp 407–411
Publication Date (Web): April 11, 2003 (Article)
DOI: 10.1021/op0256183

Efficient Enantioselective Synthesis of the NMDA 2B Receptor Antagonist Ro 67-8867

Michelangelo Scalone and Pius Waldmeier*
pp 418–425
Publication Date (Web): April 04, 2003 (Article)
DOI: 10.1021/op034006v

A New Catalytic System for the Selective Aerobic Oxidation of Large Ring Cycloalkanes to Ketones

Xavier Baucherel, Isabel W. C. E. Arends, S. Ellwood, and Roger A. Sheldon*
pp 426–428
Publication Date (Web): April 04, 2003 (Article)
DOI: 10.1021/op0340199

Process Development for a Herbicide Intermediate via Catalytic Carboxylation of an Aromatic Diazonium Compound

Urs Siegrist,* Thomas Rapold, and Hans-Ulrich Blaser
pp 429–431
Publication Date (Web): March 13, 2003 (Technical Note)
DOI: 10.1021/op025621m

The Asymmetric Synthesis of (3S,4R,5S)-3-Amino-4,5-O-isopropylidenedioxycyclopentene

Barry M. Trost* and Mark T. Sorum
pp 432–435
Publication Date (Web): March 01, 2003 (Technology Report)
DOI: 10.1021/op025611l

Large-Scale Negishi Coupling as Applied to the Synthesis of PDE472, an Inhibitor of Phosphodiesterase Type 4D

Paul W. Manley,* Murat Acemoglu,*§ Wolfgang Marterer,§ and Werner Pachinger§
pp 436–445
Publication Date (Web): April 04, 2003 (Technology Report)
DOI: 10.1021/op025615q

Letters to the Editor

Safety and Environmental Report

A. M. van den Braken
p 446
Publication Date (Web): May 01, 2003 (Communication to Editor)
DOI: 10.1021/op030015s

Additions and Corrections

Some Items of Interest to Process R&D Chemists and Engineers

Trevor Laird,* Stephen A. Hermitage, and Ulf Tilstam
p 447
Publication Date (Web): April 17, 2003 (Addition/Correction)
DOI: 10.1021/op030017c