Reduction of acyl enolates of alpha-substituted beta-keto esters by bakers' yeast.
Enol esters of 2-substituted-3-oxoalkanoates of (Z)-configuration were reduced by bakers' yeast to chiral 2-substituted-3-hydroxyalkanoates. The syn-selectivities of this reaction increased compared with those of the reduction of the corresponding racemic keto esters. The reaction may proceed via an asymmetric hydrolysis of the enol esters, followed by the reduction of the resulting carbonyl group.
Ohta
H
H
Department of Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi 3-14-1, Kohoku-ku, Yakohama 223, Japan.
Kobayashi
N
N
Sugai
T
T
D004952:Esters / Q000737:chemistry*; D006868:Hydrolysis; D007651:Keto Acids / Q000737:chemistry*; D010084:Oxidation-Reduction; D012441:Saccharomyces cerevisiae / Q000737:chemistry*; D013379:Substrate Specificity
D004952:Esters; D007651:Keto Acids