TY - JOUR
T1 - Baker's Yeast: improving the D-stereoselectivity in reduction of 3-oxo esters
AU - Madsen, Jørgen Øgaard
AU - Madsen, Jørgen Øgaard
AU - Madsen, Jørgen Øgaard
PY - 1999
Y1 - 1999
N2 - 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.
AB - 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.
U2 - 10.1016/S0957-4166(99)00025-7
DO - 10.1016/S0957-4166(99)00025-7
M3 - Journal article
SN - 0957-4166
VL - 10
SP - 551
EP - 559
JO - Tetrahedron: Asymmetry
JF - Tetrahedron: Asymmetry
IS - 3
ER -