Abstract
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.
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