Asymmetric Catalysis on Industrial Scale: Challenges, Approaches, and Solutions

General description

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 Nobel prizewinner W.S. Knowles, will also heighten the status of industrial catalyst specialists working in the exciting field of enantioselective catalysis.

Table of Contents

Introduction
I: NEW PROCESSES FOR EXISTING ACTIVE COMPOUNDS.
1. Asymmetric Hydrogenations� The Monsanto _L-Dopa Process
2. The Other _L-Dopa Process
3. The Chiral Switch of Metolachlor: The Development of a Large-Scale Enantioselective Catalytic Process
4. Enantioselective Hydrogenation: Towards a Large-Scale Total Synthesis of (R,R,R)-a-Tocopherol
5. Comparison of Four Technical Synthesis of Ethyl (R)-2-Hydroxy-4-Phenylbutrate
6. Biocatalytic Approaches for the Large-Scale Production of Asymmetric Synthons
7. 7-Aminocephalosporanic Acid-Chemical Versus Enzymatic Production Process
8. Methods for the Enantioselective Biocatalytic Pro duction of L-Amino Acids on an Industrial Scale
II: NEW CATALYSTS FOR EXISTING ACTIVE COMPOUNDS.
1. The Large-Scale Biocatalytic Synthesis of Enantiopure Cyanohydrins
2. Industrialization Studies of the Jacobsen-Hydrolytic Kinetic Resolution of Epichlorohydrin
3. Scale-up Studies in Asymmetric Transfer Hydrogenation
4. Practical Applications of Biocatalysis for the Manufacture of Chiral Alcohols such as (R)-1,3-Butanediol by Stereospecific Oxidoreduction
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
III: ADAPTATION OF EXISTING CATALYSTS FOR IMPORTANT BUILDING BLOCK.
1. Synthesis of Unnatural Amino Acids
2. The Application of DuPHOS Rhodium(I) Catalysts for Commercial Scale Asymmetric Hydrogenation
3. Liberties and Constraints in the Development of Asymmetric Hydrogenations on a Technical Scale
4. Large-Scale Applications of Biocatalysis in the Asymmetric Synthesis of Laboratory Chemicals
IV: PROCESSES FOR NEW CHEMICAL ENTITIES (NCE).
1. Development of an Efficient Synthesis of Chiral 2-Hydroxy Acids
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
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
4. Multi-Kilo Resolution of XU305, a Key Intermediate to the Platelet Glycoprotein IIb/IIIa Receptor Antagonist Roxifiban Via Kinetic and Dynamic Enzymatic Resolution
5. Protease-Catalyzed Preparation of (S)-2-[(tert-Butylsulfonyl)methyl]-hydrocinnamic Acid for Renin Inhibitor RO0425892
6. Protease-Catalyzed Preparation of Chiral 2-Isobutyl Succinic Acid Derivatives for Collagenase Inhibitor RO0319790 .
7. An Innovative Asymmetric Sulfide Oxidation: The Process Development History Behind the New Antiulcer Agent Esomeprazole).
8. Development of a Biocatalytic Process for the Resolution of (R)- and (S)-Ethyl-3-amino-4-pentynoate Isomers Using Enzyme Penicillin G Amidohydrolase
Subject Index.