Synthesis of 1,5-bifunctionalized optically active 3-pentanol as a reversible chiral building block. Asymmetric reduction of 4-(1,3-dithian-2-yl)-3-oxobutanoates with fermenting bakers' yeast.

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概要

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• Bakers' yeast reduction of a homologous series of 4-(1,3-dithian-2-yl)-3-oxobutanoates to the corresponding chiral 4-(1,3-dithian-2-yl)-3-hydroxybutanoates was investigated. A shift in enantiomeric excess, stereochemistry, and chemical yield of the reduction product was observed as the size of the ester alkoxyl group was changed. The kind of bakers' yeast (raw or dry) and reaction conditions also affected the optical purity and chemical yield of the product. These studies showed that the reduction of methyl 4-(1,3-dithian-2-yl)-3-oxobutanoate with the raw yeast in the absence of additives was most efficient, giving methyl (<I>S</I>)-4-(1,3-dithian-2-yl)-3-hydroxybutanoate with 77% ee in 37% yield.

• 公益社団法人 日本化学会の論文

著者

• Ohkawa Kazuhiko

  Department of Applied Chemistry, Faculty of Engineering, Kansai University

関連論文

• Synthesis of 1,5-bifunctionalized optically active 3-pentanol as a reversible chiral building block. Asymmetric reduction of 4-(1,3-dithian-2-yl)-3-oxobutanoates with fermenting bakers' yeast.

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