Stereochemical control in microbial reduction. 9. Diastereoselective reduction of 2-alkyl-3-oxobutanoate with bakers' yeast.

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概要

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• Bakers' yeast reduces esters of 2-alkyl-3-oxobutanoic acid (CH<SUB>3</SUB>COCHRCO<SUB>2</SUB>R′; R=methyl, ethyl, propyl, propargyl, and allyl) into the corresponding (<I>S</I>)-hydroxy esters with exclusive stereoselectivity, while the configuration at the 2-position of the hydroxy esters is either <I>S</I> (anti) or <I>R</I> (syn) depending on the structure of the alkoxyl group in the carboalkoxyl moiety of the ester. Oftenly, the stereoselectivity with respect to the 2-position is not satisfactory. In general, the reduction of <I>t</I>-butyl esters exerts predominancy in the products, whereas that of 1,1-dimethylpropyl esters exerts the syn predominancy. A marked difference between these two esters in diastereoselectivity is discussed from the view point of plausible conformations of the esters.

• 公益社団法人 日本化学会の論文

著者

• Ohno Atsuyoshi

  Institute For Chemical Research Kyoto Univ.

• Oka Shinzaburo

  Institute For Chemical Research Kyoto University

• Miyai Takehiko

  Institute For Chemical Research Kyoto University

• Nakamura Kaoru

  Department of Chemistry, Shiga University of Medical Science

• Nagar Ashish

  Institute for Chemical Research, Kyoto University

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