Journal
TETRAHEDRON
Volume 68, Issue 2, Pages 523-528Publisher
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
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Funding
- 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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