Asymmetric Reduction of [alpha]-Keto Esters and [alpha]-Diketones with a Bakers' Yeast Keto Ester Reductase

Optically pure α-hydroxy esters and α-hydroxy ketones have been synthesized by the reduction of the corresponding ketones with a keto ester reductase isolated from bakers' yeast (YKER-I). The reduction of α-keto esters affords the corresponding (S)- or (R)-hydroxy esters selectively, where the...

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Bibliographic Details
Published in:Bulletin of the Chemical Society of Japan 1999-01, Vol.72 (1), p.99
Main Authors: Kawai, Yasushi, Hida, Kouichi, Tsujimoto, Munekazu, Kondo, Shin-ichi, Kitano, Kazutada, Nakamura, Kaoru, Ohno, Atsuyoshi
Format: Article
Language:English
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Summary:Optically pure α-hydroxy esters and α-hydroxy ketones have been synthesized by the reduction of the corresponding ketones with a keto ester reductase isolated from bakers' yeast (YKER-I). The reduction of α-keto esters affords the corresponding (S)- or (R)-hydroxy esters selectively, where the stereochemical course depends on the chain length of the alkyl substituent on the carbonyl group. An α-keto short alkanoic ester affords the corresponding (S)-hydroxy ester, whereas a long alkanoate yields the corresponding (R)-hydroxy ester. The reduction of α-diketones affords the corresponding (S)-2-hydroxy ketones regio- and stereoselectively.
ISSN:0009-2673
1348-0634