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.
Madsen, J. Ø., Madsen, J. Ø., & Madsen, J. Ø. (1999). Baker's Yeast: improving the D-stereoselectivity in reduction of 3-oxo esters. Tetrahedron: Asymmetry, 10(3), 551-559. https://doi.org/10.1016/S0957-4166(99)00025-7