Asymmetric Reduction ofα-Keto Esters andα-Diketones with a Bakers’ Yeast Keto Ester Reductase

Autor:	Munekazu Tsujimoto, Kaoru Nakamura, Shin-ichi Kondo, Kouichi Hida, Yasushi Kawai, Kazutada Kitano, Atsuyoshi Ohno
Rok vydání:	1999
Předmět:	chemistry.chemical_classification Chain length chemistry.chemical_compound chemistry Stereochemistry Substituent General Chemistry Reductase Bakers Yeast Carbonyl group Yeast Alkyl
Zdroj:	Bulletin of the Chemical Society of Japan. 72:99-102
ISSN:	1348-0634 0009-2673
DOI:	10.1246/bcsj.72.99
Popis:	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.
Databáze:	OpenAIRE
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