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
This publication has 10 references indexed in Scilit:
- Diastereo- and enantioselective reduction of α,β-diketodithiane with the baker's yeastTetrahedron Letters, 1985
- Stereochemical control of microbial reduction. 2. Reduction of β-keto esters by immobilized bakers' yeastTetrahedron Letters, 1985
- Synthesis of the two enantiomeric forms of 5-hexadecanolide proposed pheromone component from Vespa orientalisTetrahedron Letters, 1983
- Non-carbohydrate based synthesis of natural LTB4Tetrahedron Letters, 1983
- On the steric course of the addition of diallylzinc onto α,β-dialkoxy chiral carbonyl compounds: stereospecific synthesis of 2,6-dideoxysugars of theTetrahedron Letters, 1982
- Stereospecific synthesis of isomeric 4-substituted 9-(2,3-dihydroxybutyl)adeninesCollection of Czechoslovak Chemical Communications, 1982
- The immobilization of microbial cells, subcellular organelles, and enzymes in calcium alginate gelsBiotechnology & Bioengineering, 1977
- Absolute configurations of the (–)-erythro and (–)-threo-2,3-dihydroxybutyric acidsCanadian Journal of Chemistry, 1969
- Intramolecular Hydrogen Bonds. VI. The Characteristic Infrared OH Spectra of Isomeric Ethyl α, β-Dihydroxy-carboxylates and Their GeometriesBulletin of the Chemical Society of Japan, 1965
- Specification of the stereospecificity of some oxido-reductases by diamond lattice sectionsPure and Applied Chemistry, 1964