4.4 Article

Enantioselective reduction and deracemisation using the non-conventional yeast Pichia glucozyma in water/organic solvent biphasic systems: preparation of (S)-1,2-diaryl-2-hydroxyethanones (benzoins)

Journal

TETRAHEDRON
Volume 68, Issue 2, Pages 523-528

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2011.11.014

Keywords

Benzoin; Deracemisation; Pichia glucozyma; Benzil; Dehydrogenase; Stereoselective reduction; Two-liquid-phase system

Funding

  1. MICINN (Spanish Ministry of Science and Innovation) [CTQ2009-11801]

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Water/organic solvent two-liquid-phase systems have been successfully applied in the synthesis of enantiomerically pure (S)-benzoin through two different methodologies catalysed by whole cells from the non-conventional yeast Pichia glucozyma: the stereoselective monoreduction of benzil and the deracemisation of benzoin. The presence of the organic solvent influences the redox systems implied in the reactions, avoiding the formation of the corresponding diols, increasing the enantioselectivity and allowing the easy isolation of the products in high yields and excellent enantiomeric excesses. The use of both strategies has been extended to the preparation of different chiral benzoin derivatives. (C) 2011 Elsevier Ltd. All rights reserved.

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