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Asymmetric Catalysis on Industrial Scale: Challenges, Approaches and Solutions
Hans Ulrich Blaser (Editor), Elke Schmidt (Editor)
ISBN: 978-3-527-30631-2
Hardcover
480 pages
January 2004
US $255.00 Add to Cart

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  • Description
  • Table of Contents
  • Author Information
  • Reviews
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 (Rüdiger 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 Gröger & 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-Jürgen 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.