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Enantioselective Synthesis of Both Enantiomers of Various Propargylic Alcohols by Use of Two Oxidoreductases

  1. Thomas Schubert1,
  2. Werner Hummel2,
  3. Maria-Regina Kula2,
  4. Michael Müller1

Article first published online: 25 OCT 2001

DOI: 10.1002/1099-0690(200111)2001:22<4181::AID-EJOC4181>3.0.CO;2-T

Issue

European Journal of Organic Chemistry

European Journal of Organic Chemistry

Volume 2001, Issue 22, pages 4181–4187, November 2001

Additional Information

How to Cite

Schubert, T., Hummel, W., Kula, M.-R. and Müller, M. (2001), Enantioselective Synthesis of Both Enantiomers of Various Propargylic Alcohols by Use of Two Oxidoreductases. Eur. J. Org. Chem., 2001: 4181–4187. doi: 10.1002/1099-0690(200111)2001:22<4181::AID-EJOC4181>3.0.CO;2-T

Author Information

  1. 1

    Institut für Biotechnologie 2, Forschungszentrum Jülich GmbH 52425 Jülich, Germany, Fax: (internat.) +49 2461/613870

  2. 2

    Institut für Enzymtechnologie der Heinrich-Heine Universität Düsseldorf auf dem Gelände der Forschungszentrum Jülich GmbH, 52426 Jülich, Germany

Publication History

  1. Issue published online: 25 OCT 2001
  2. Article first published online: 25 OCT 2001
  3. Manuscript Received: 26 MAR 2001

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Keywords:

  • Alcohols;
  • Alkynones;
  • Asymmetric catalysis;
  • Oxidoreductases;
  • Reductions

Abstract

The oxidoreductases Lactobacillus brevis alcohol dehydrogenase (LBADH) and Candida parapsilosis carbonyl reductase (CPCR) are suitable catalysts for the reduction of ketones to afford enantiopure sec. alcohols. A broad variety of alkynones (1, 3, and 5) are accepted as substrates and the corresponding propargylic alcohols (2, 4, and 6) are obtained in good yield and excellent enantiomeric excess. By changing the steric demand of the substituents the ee values can be adjusted and even the configurations of the products can be altered.

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