Stereocontrolled Reduction of Alpha-Methyl Beta-Ketoesters by Geotrichum Candidum
- 1 January 1990
- journal article
- research article
- Published by Taylor & Francis in Biocatalysis
- Vol. 3 (1-2) , 85-93
- https://doi.org/10.3109/10242429008992051
Abstract
The conditions of the reduction of racemic ethyl 2-methyi-3-oxobutanoate by the mould Geotrichum candidum have been investigated in order to produce exclusively the corresponding (2S, 3S) anti hydroxyester. The alteration of the syn/anti hydroxyester ratio previously observed is the result of an interconversion equilibrium involving the oxoester. The syn ester formation is inhibited by ageing the biomass in water before use, or by effecting the reduction in the presence of sodium chloride. Optimized conditions are described allowing the production of the anti ester in high yield and high optical purity.Keywords
This publication has 15 references indexed in Scilit:
- (S)‐O‐acetyllactyl chloride – a versatile chiral auxiliary in stereodifferentiation of enantiomeric flavor componentsJournal of High Resolution Chromatography, 1987
- Diastereo- and enantioselective microbiological reduction of 2-methyl 3-oxoalkanoatesTetrahedron Letters, 1987
- Diastereoselective and enantioselective microbial reduction of cyclic alpha-alkyl beta-ketoestersTetrahedron Letters, 1986
- Syntheses of the Sex-Attractant of Pine SawfliesBulletin of the Chemical Society of Japan, 1984
- The Aldol Addition ReactionPublished by Elsevier ,1984
- Synthetic studies of polyene macrolides, synthesis of a C29–37 fragment for amphotericin B and nystatinTetrahedron Letters, 1982
- Stereoselektive Synthese von Alkoholen, IX. Absolute Konfiguration von StegobinonEuropean Journal of Inorganic Chemistry, 1981
- Über die Stereospezifität der α‐Alkylierung von β‐Hydroxycarbonsäureestern. Vorläufige MitteilungHelvetica Chimica Acta, 1979
- Asymmetric reductinon of carbonyl compounds by yeast. II. Preparation of optically active α- and β-hydroxy carboxylic acid derivativesAustralian Journal of Chemistry, 1976
- .alpha.-Methoxy-.alpha.-trifluoromethylphenylacetic acid, a versatile reagent for the determination of enantiomeric composition of alcohols and aminesThe Journal of Organic Chemistry, 1969