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Organic Chemistry Reference from C.H.I.P.S.

Asymmetric Catalysis on Industrial Scale
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
    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 and 3-chloro-1,2-propanediol and Related Halohydrins

  3. Adaptation of Existing Catalysts for Important Building Blocks
    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

  4. Processes for New Chemical Entities
    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

Index

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Asymmetric Catalysis on Industrial Scale
edited by H.U. Blaser
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