Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions

Abstract

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.