Baker's Yeast: improving the D-stereoselectivity in reduction of 3-oxo esters

Jørgen Øgaard Madsen, Jørgen Øgaard Madsen, Jørgen Øgaard Madsen

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    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. (C) 1999 Elsevier Science Ltd. All rights reserved.
    Original languageEnglish
    JournalTetrahedron: Asymmetry
    Issue number3
    Pages (from-to)551-559
    Publication statusPublished - 1999

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