edited by H.U. Blaser

Asymmetric Catalysis on Industrial Scale shows organic chemists working in process development that enantioselective catalysis is suitable for the large-scale production of enantioenriched intermediates. I

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.

Contents

1. 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)-u-Tocopherol
   5. Comparison of Four Technical Syntheses of Ethyl (R)-2-Hydroxy-4-Phenylbutyrate
   6. Biocatalytic Approaches for the Large-Scale Production of Asymmetric Synthons
   7. 7-Aminocepholasporanic Acid - Chemical vs. Enzymatic Production Process
   8. Methods for the Enantioselective Biocatalytic Production of L-Amino Acids on an Industrial Scale

2. New Catalysts for Existing Active Compounds
   9. The Large-Scale Biocatalytic Synthesis of Enantiopure Cyanohydrins
   10. Industrialization Studies of the Jacobsen Hydrolytic Kinetic Resolution of Epichlorohydrin
   11. Scale-up Studies in Asymmetric Transfer Hydrogenation
   12. Practical Applications of Biocatalysis for the Manufacture of Chiral Alcohols such as (R)-1,3-butanediol by Stereospecific Oxidoreduction
   13. Production of Chiral C3 and C4 Units via Microbial Resolution of 2,3-dichloro-1-propanol and 3-chloro-1,2-propanediol and Related Halohydrins

3. Adaptation of Existing Catalysts for Important Building Blocks
   14. Synthesis of Unnatural Amino Acids
   15. The Application of DuPHOS Rhodium(I) Catalysts for Commercial Scale Asymmetric Hydrogenation
   16. Liberties and Constraints in the Development of Asymmetric Hydrogenations on a Technical Scale
   17. Large-Scale Applications of Biocatalysis in the Asymmetric Synthesis of Laboratory Chemicals

4. Processes for New Chemical Entities
   18. Development of an Efficient Synthesis of Chiral 2-Hydroxy Acids
   19. Factors Influencing the Application of Literature Methods Toward the Preparation of a Chiral trans-Cyclopropane Carboxylic Acid Intermediate During Development of a Melatonin Agonist
   20. 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
   21. Multi-Kilo Resolution of XU305, a key intermediate to the platelet glycoprotein IIb/IIIa receptor antagonist roxifiban via kinetic and dynamic enzymatic resolution
   22. Protease-Catalyzed Preparation of (S)-2-[(tert-Butylsulfonyl)methyl]-hydrocinnamic Acid for Renin Inhibitor RO0425892
   23. Protease-Catalyzed Preparation of Chiral 2-Isobutyl Succinic Acid Derivatives for Collagenase Inhibitor RO0319790
   24. An Innovative Asymmetric Sulfide Oxidation: The Process Development History Behind the New Antiulcer Agent Esomeprazole
   25. Development of a Biocatalytic Process for the Resolution of (R)- and (S)-Ethyl 3-amino-4-pentynoate Isomers Using Enzyme Penicillin G Amidohydrolase

Index

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