Chapter 4. Dynamic Kinetic Resolution for the Synthesis of Esters, Amides and Acids Using Lipases

  1. John Whittall10 and
  2. Peter Sutton11
  1. Kam Loon Fow1,
  2. Yongzhong Zhu1,
  3. Gaik Khuan Chuah1,
  4. Stephan Jaenicke1,
  5. S. F. G. M. van Nispen2,
  6. J. van Buijtenen2,
  7. J. A. J. M. Vekemans2,
  8. J. Meuldijk2,
  9. L. A. Hulshof2,
  10. Michael Page3,
  11. John Blacker4,
  12. Matthew Stirling3,
  13. Soo-Byung Ko5,
  14. Mahn-Joo Kim5,
  15. Jaiwook Park5,
  16. Stéphane Gastaldi6,
  17. Gérard Gil7,
  18. Michèle P. Bertrand6,
  19. A. H. Kamaruddin8,
  20. Matthew Truppo9,
  21. David Pollard9,
  22. Jeffrey Moore9 and
  23. Paul Devine9

Published Online: 15 DEC 2009

DOI: 10.1002/9780470748589.ch4

Practical Methods for Biocatalysis and Biotransformations

Practical Methods for Biocatalysis and Biotransformations

How to Cite

Fow, K. L., Zhu, Y., Chuah, G. K., Jaenicke, S., van Nispen, S. F. G. M., van Buijtenen, J., Vekemans, J. A. J. M., Meuldijk, J., Hulshof, L. A., Page, M., Blacker, J., Stirling, M., Ko, S.-B., Kim, M.-J., Park, J., Gastaldi, S., Gil, G., Bertrand, M. P., Kamaruddin, A. H., Truppo, M., Pollard, D., Moore, J. and Devine, P. (2009) Dynamic Kinetic Resolution for the Synthesis of Esters, Amides and Acids Using Lipases, in Practical Methods for Biocatalysis and Biotransformations (eds J. Whittall and P. Sutton), John Wiley & Sons, Ltd, Chichester, UK. doi: 10.1002/9780470748589.ch4

Editor Information

  1. 10

    Manchester Interdisciplinary Biocentre, University of Manchester, United Kingdom

  2. 11

    GlaxoSmithKline, Synthetic Chemistry, Gunnels Wood Road, Stevenage, Hertfordshire SG1 2NY, UK

Author Information

  1. 1

    Department of Chemistry, National University of Singapore, Kent Ridge, Singapore 119260, Republic of Singapore

  2. 2

    Eindhoven University of Technology, Laboratory of Macromolecular and Organic Chemistry, PO Box 513, 5600 MB Eindhoven, The Netherlands

  3. 3

    Department of Chemical and Biological Sciences, The University of Huddersfield, Huddersfield, HD1 3DH, UK

  4. 4

    NPIL Pharma Ltd, Leeds Road, Huddersfield, HD1 9GA, UK

  5. 5

    Department of Chemistry, Pohang University of Science and Technology (POSTECH), San-31, Hyojadong, Pohang 790-784, Korea

  6. 6

    Laboratoire de Chimie Moléculaire Organique, LCP UMR 6264, Boite 562, Université Paul Cézanne, Aix-Marseille III, Faculté des Sciences St Jéroôme, Avenue Escadrille Normandie-Niemen, 13397 Marseille Cedex 20, France

  7. 7

    Laboratoire de Stéréochimie Dynamique et Chiralité, ISM2, UMR 6263, Université Paul Cézanne, Aix-Marseille III, Faculté des Sciences St Jéroôme, Avenue Escadrille Normandie-Niemen, 13397 Marseille Cedex 20, France

  8. 8

    School of Chemical Engineering, Engineering Campus, Universiti Sains Malaysia, Seri Ampangan, 14300, Nibong Tebal, Penang, Malaysia

  9. 9

    Process Research, Merck Research Laboratories, Merck & Co. Inc., Rahway, NJ, USA

Publication History

  1. Published Online: 15 DEC 2009
  2. Published Print: 18 DEC 2009

ISBN Information

Print ISBN: 9780470519271

Online ISBN: 9780470748589

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Keywords:

  • dynamic kinetic resolution for ester, amide and acid synthesis using lipases;
  • one-pot dynamic kinetic resolution (DKR) of (–)-1-phenylethanol lipase esterification in presence of zeolite beta;
  • Procedure 1 - synthesis of (R)-1-phenylethyl octanoate;
  • Procedure 2 - hydrolysis of (R)-1-phenylethyl octanoate;
  • DKR method, applied to secondary alcohols;
  • synthesis of (R)-butyrate esters of secondary alcohols by DKR;
  • Bis(tetrafluorosuccinato)-bridged Ru(II) complex 1;
  • dynamic kinetic resolution of 6,7-dimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline;
  • dynamic kinetic resolution of primary amines with recyclable palladium nanocatalyst (Pd/AlO(OH)) for racemization;
  • chemoenzymatic dynamic kinetic resolution of (S)-Ibuprofen

Summary

This chapter contains sections titled:

  • Dynamic Kinetic Resolution of 1-Phenylethanol by Immobilized Lipase Coupled with In Situ Racemization over Zeolite Beta

  • Synthesis of the (R)-Butyrate Esters of Secondary Alcohols by Dynamic Kinetic Resolution Employing a Bis(tetrafluorosuccinato)-bridged Ru(II) Complex

  • Dynamic Kinetic Resolution 6,7-Dimethoxy-1-methyl-1,2,3,4-tetrahydroisoquinoline

  • Dynamic Kinetic Resolution of Primary Amines with a Recyclable Palladium Nanocatalyst (Pd/AlO(OH)) for Racemization

  • Dynamic Kinetic Resolution of Amines Involving Biocatalysis and In Situ Free-radical-mediated Racemization

  • Chemoenzymatic Dynamic Kinetic Resolution of (S)-Ibuprofen

  • Dynamic Kinetic Resolution Synthesis of a Fluorinated Amino Acid Ester Amide by a Continuous Process Lipase-mediated Ethanolysis of an Azalactone

  • References