Chapter 5. Chemoenzymatic Deracemization Processes

  1. Dr. Giacomo Carrea,
  2. Dr. Sergio Riva
  1. Belén Martín-Matute,
  2. Jan-E. Bäckvall

Published Online: 21 FEB 2008

DOI: 10.1002/9783527621729.ch5

Book Title

Organic Synthesis with Enzymes in Non-Aqueous Media

Organic Synthesis with Enzymes in Non-Aqueous Media

Additional Information

How to Cite

Martín-Matute, B. and Bäckvall, J.-E. (2008) Chemoenzymatic Deracemization Processes, in Organic Synthesis with Enzymes in Non-Aqueous Media (eds G. Carrea and S. Riva), Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim, Germany. doi: 10.1002/9783527621729.ch5

Editor Information

  1. Istituto di Chimica del Riconoscimento Molecolare, C.N.R., Via Mario Bianco 9, 20131 Milano, Italy

Author Information

  1. Stockholm University, Department of Organic Chemistry, Arrhenius Laboratory, 10691 Stockholm, Sweden

Publication History

  1. Published Online: 21 FEB 2008
  2. Published Print: 13 FEB 2008

ISBN Information

Print ISBN: 9783527318469

Online ISBN: 9783527621729

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CHAPTER TOOLS

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Keywords:

  • chemoenzymatic deracemization processes;
  • dynamic kinetic resolution (DKR);
  • cyclic deracemizations

Summary

This chapter contains sections titled:

  • Introduction

    • Asymmetric Synthesis Methods

    • Dynamic Kinetic Resolution (DKR)

    • Cyclic Deracemizations

  • Dynamic Kinetic Resolution

    • Base-Catalyzed Racemization

      • DKR of Thioesters

      • DKR of Activated Esters

      • DKR of Oxazolones

      • DKR of Hydantoins

      • DKR of Acyloins

    • Acid-Catalyzed Racemization

    • Racemization through Continuous Reversible Formation–Cleavage of the Substrate

      • DKR of Cyanohydrins

      • DKR of Hemithioacetals

    • Racemization Catalyzed by Aldehydes

    • Enzyme-Catalyzed Racemization

    • Racemization through SN2 Displacement

    • Radical Racemization

    • Metal-Catalyzed Racemization

      • DKR of Allylic Acetates and Allylic Alcohols

      • DKR of sec-Alcohols

      • DKR of Amines

    • Other Racemization Methods

      • DKR of 5-Hydroxy-2-(5H)-Furanones

      • DKR of Hemiaminals

      • DKR of 8-Amino-5,6,7,8-Tetrahydroquinoline

  • Cyclic Deracemizations

    • Chemoenzymatic Cyclic Deracemizations

      • Cyclic Deracemizations of Amino Acids

      • Chemoenzymatic Cyclic Deracemizations of Hydroxy Acids

      • Chemoenzymatic Cyclic Deracemizations of Amines

    • Biocatalyzed Deracemizations

  • Concluding Remarks

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