Highly Enantioselective Reduction of Ethyl 2-Acyloxy-3-oxobutanoate with Immobilized Baker’s Yeast
- 1 October 1986
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 59 (10) , 3185-3188
- https://doi.org/10.1246/bcsj.59.3185
Abstract
Reduction of ethyl 2-acetoxy-3-oxobutanoate (4a) with immobilized baker’s yeast in calcium alginate gel gave a 18 : 19 : 63 mixture of ethyl (2R,3S)- and (2S,3S)-2-acetoxy-3-hydroxybutanoates and ethyl (2S,3S)-2,3-dihydroxybutanoate each with >95% e.e. in 58% yield. A similar treatment of a 2-benzoyloxy analog of 4a afforded a 6 : 94 mixture of ethyl (2R,3S)- and (2S,3S)-2-benzoyloxy-3-hydroxybutanoates (>95% e.e.) in 70% yield. Their absolute configurations were determined by comparison with authentic (2R,3S)- and (2S,3S)-2,3-dihydroxybutanoic acids. Effects of the immobilization and the pH of culture solution on the product ratio are also discussed.Keywords
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