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A Study of the Stereocontrolled Reduction of Aliphatic β-Ketoesters by Geotrichum candidum
Authors:D Buisson  R Azerad  C Sanner  M Larcheveque
Abstract:The conditions necessary to reduce stereoselectively aliphatic beta-ketoesters by G. candidum have been investigated. Ageing of the mycelium allowed a practical preparation of optically pure (R)-ethyl 3-hydroxybutanoate, as a result of stereoselective reduction, enantioselective metabolism and stereoisomer interconversion. The stereoconversion of 3S-hydroxybutanoate into the 3R-enantiomer via 3-oxoester formation has been demonstrated to be a determining factor in the building of the optical purity of the resulting product. Enantioselective preparations of higher homologous 3R-hydroxyesters are described.
Keywords:3-Oxoesters  β-ketoesters  3-hydroxyesters  stereoselective reduction  microbial oxidoreduction  Geotrichum candidum  (R)-ethyl 3-hydroxybutanoate  (R)-ethyl 3-hydroxypentanoate  (S)-ethyl 3-hydroxy-4-methylpentanoate  (R)-ethyl 3-hydroxyhexanoate  (R)-ethyl 3-hydroxyoctanoate  (R)-ethyl 3-hydroxydecanoate
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