Baker's yeast: improving the d-stereoselectivity in reduction of 3-oxo esters

The stereoselectivity of baker's yeast in the reduction of ethyl 3-oxopentanoate was shifted towards the corresponding ( R)-hydroxy ester by sugar, heat treatment and allyl alcohol. The highest enantiomeric excesses obtained with baker's yeast with a good reduction capacity, 92–97%, were a...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 1999-02, Vol.10 (3), p.551-559
Main Authors: Dahl, Allan C, Fjeldberg, Morten, Madsen, Jørgen Øgaard
Format: Article
Language:English
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Summary:The stereoselectivity of baker's yeast in the reduction of ethyl 3-oxopentanoate was shifted towards the corresponding ( R)-hydroxy ester by sugar, heat treatment and allyl alcohol. The highest enantiomeric excesses obtained with baker's yeast with a good reduction capacity, 92–97%, were achieved by combining allyl alcohol and sugar; heat treatment did not increase the stereoselectivity further. With the use of this technique, ethyl ( R)-3-hydroxyhexanoate, >99% ee, and ethyl ( S)-4-chloro-3-hydroxybutanoate, 82–90% ee, were produced from the corresponding esters, and for the first time an excess of the ( R)-enantiomer of ethyl 3-hydroxybutanoate was obtained with ordinary baker's yeast.
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(99)00025-7