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Asymmetric Catalysis on Industrial Scale

Challenges, Approaches and Solutions



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Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions
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Edited by two of the experts in the field, the central aim is to show organic chemists working in process development that enantioselective catalysis is suitable for the large-scale production of enantioenriched intermediates. In so doing, it is equally a source of information and inspiration for academic research, and, with its contribution by Noble prizewinner W. S. Knowles, will also heighten the status of industrial catalyst specialists working in the exciting field of enantioselective catalysis. Some 25 contributions from top industrial researchers around the world present case studies on the development of the widest possible range of large-scale enantioselective processes, featuring stereoselective production processes of fine-chemicals, agrochemicals and pharmaceuticals. Clearly structured according to the nature of the task, this handbook adopts a problem-driven approach such that readers can easily find how colleagues have dealt with a similar situation.

Table of Contents

List of Contributors.Introduction (Hans-Ulrich Blaser & Elke Schmidt).I: NEW PROCESSES FOR EXISTING ACTIVE COMPOUNDS.1. Asymmetric Hydrogenations- The Monsanto L-Dopa Process (William S. Knowles).2. The Other L-Dopa Process (Rudiger Selke).3. The Chiral Switch of Metolachlor: The Development of a Large-Scale Enantioselective Catalytic Process (Hans-Ulrich Blaser, et al.).4. Enantioselective Hydrogenation: Towards a Large-Scale Total Synthesis of (R,R,R)-a-Tocopherol (Thomas Netscher, et al.).5. Comparison of Four Technical Synthesis of Ethyl (R)-2-Hydroxy-4-Phenylbutrate (Hans-Ulrich Blaser, et al.).6. Biocatalytic Approaches for the Large-Scale Production of Asymmetric Synthons (Nicholas M. Shaw, et al.).7. 7-Aminocephalosporanic Acid-Chemical Versus Enzymatic Production Process (Thomas Bayer).8. Methods for the Enantioselective Biocatalytic Pro duction of L-Amino Acids on an Industrial Scale (Harald Groger & Karlheinz Drauz).II: NEW CATALYSTS FOR EXISTING ACTIVE COMPOUNDS.1. The Large-Scale Biocatalytic Synthesis of Enantiopure Cyanohydrins (Peter Poechlauer, et al.).2. Industrialization Studies of the Jacobsen-Hydrolytic Kinetic Resolution of Epichlorohydrin (Larbi Aouni, et al.).3. Scale-up Studies in Asymmetric Transfer Hydrogenation (John Blacker & Juliette Martin).4. Practical Applications of Biocatalysis for the Manufacture of Chiral Alcohols such as (R)-1,3-Butanediol by Stereospecific Oxidoreduction (Akinobu Matsuyama & Hiroaki Yamamoto).5. Production of Chiral C3 and C4 Units via Microbial Resolution of 2,3-Dichloro-1-propanol, 3-Chloro-1,2-propanediol and Related Halohydrins (N. Kasai o& T. Suzuki).III: ADAPTATION OF EXISTING CATALYSTS FOR IMPORTANT BUILDING BLOCK.1. Synthesis of Unnatural Amino Acids (David J. Ager & Scott A. Laneman.).2. The Application of DuPHOS Rhodium(I) Catalysts for Commercial Scale Asymmetric Hydrogenation (Christopher J. Cobley, et al.).3. Liberties and Constraints in the Development of Asymmetric Hydrogenations on a Technical Scale (John F. McGarrity, et al.).4. Large-Scale Applications of Biocatalysis in the Asymmetric Synthesis of Laboratory Chemicals (Roland Wohlgemuth).IV: PROCESSES FOR NEW CHEMICAL ENTITIES (NCE).1. Development of an Efficient Synthesis of Chiral 2-Hydroxy Acids (Junhua Tao & Kevin McGee).2. Factors Influencing the Application of Literature Methods Toward the Preparation of a Chiral trans-Cyclopropane Carboxylic Acid Intermediate During Development of a Melatonin Agonist (Ambarish K. Singh, et al.).3. Hetero Diels-Alder-Biocatalysis Approach for the Synthesis of (S)-3-[2-{(Methylsulfonyl)oxy}ethoxy]-4-(triphenylmethoxy)-1-butanol Methanesulfonate: Successful Application of an Enzyme Resolution Process (Jean-Claude Caille, et al.).4. Multi-Kilo Resolution of XU305, a Key Intermediate to the Platelet Glycoprotein IIb/IIIa Receptor Antagonist Roxifiban Via Kinetic and Dynamic Enzymatic Resolution (Jaan A. Pesti & Luigi Anzalone).5. Protease-Catalyzed Preparation of (S)-2-[(tert-Butylsulfonyl)methyl]-hydrocinnamic Acid for Renin Inhibitor RO0425892 (Beat Wirz, et al.).6. Protease-Catalyzed Preparation of Chiral 2-Isobutyl Succinic Acid Derivatives for Collagenase Inhibitor RO0319790 (Beat Wirz, et al.).7. An Innovative Asymmetric Sulfide Oxidation: The Process Development History Behind the New Antiulcer Agent Esomeprazole (Hans-Jurgen Federsel & Magnus Larsson).8. Development of a Biocatalytic Process for the Resolution of (R)- and (S)-Ethyl-3-amino-4-pentynoate Isomers Using Enzyme Penicillin G Amidohydrolase (Ravindra S. Topgi).Subject Index.

Author Biography

Hans-Ulrich Blaser carried out this doctoral research with A. Eschenmoser at the Federal Institute of Technology (ETH) Zurich, from which he received the Ph.D. degree in 1971. Between 1971 and 1975 he held postdoctoral positions at the University of Chicago (J. Halpern), Harvard University (J.A. Osborn), and Monsanto (Zurich). During 20 years at Ciba0Geigy (1976-1996) he gained practical experience at R&D in the fine chemicals and pharmaceutical industry, which continued at Novartis (1996-1999) and at Solvias where he presently is chief technology officer. During his industrial career he has developed and implemented numerous catalytic routes for agrochemicals, pharmaceuticals and fine chemicals both as project leader and section head. His main interests are focused on (enantio) selective catalysis and the integration of catalytic steps into the syntheses of commercial products. Elke Schmidt carried out her doctoral research with Prof. Christian Wandrey at the Institute for Biotechnology (Nuclear Research Center) in Juelich. She received her Ph.D. degree in 1987 from the Institute for Chemistry of the Rheinische Friedrich Wilhelm University, Bonn. During the last 16 years at Ciba-Geigy, Norvatis and Syngenta, she held various positions in R&D, during the last 10 years in Crop Protection Research. Her main interest is focused on biotransformation, natural products discovery and fermentation development for small molecules and proteins.
Release date NZ
November 14th, 2003
Edited by Elke Schmidt Edited by Hans Ulrich Blaser
Country of Publication
Wiley-VCH Verlag GmbH
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