Preparation of Sulfur-Containing Optically Active Secondary Alcohols Based on Pichia farinosa-Catalyzed anti-Prelog-Rule Reduction as the Key Step
- 1 February 1997
- journal article
- research article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 70 (2) , 483-491
- https://doi.org/10.1246/bcsj.70.483
Abstract
A Pichia farinosa IAM 4682 mediated reduction of sulfur containing ketones afforded secondary alcohols with (R)-absolute configuration. For example, 4-(phenylthio)-2-butanone and 4-(phenylsulfonyl)-2-butanone afforded (R)-4-(phenylthio)-2-butanol (91%ee) in 90% yield and (R)-4-(phenylsulfonyl)-2-butanol (97%ee) in 94% yield, respectively. In the case that the ee of the product was not satisfactory, any contaminating (S)-enantiomer was selectively oxidized by Rhodococcus rhodochrous IFO 15564 to leave pure (R)-enantiomer. The substrate specificity of Pichia farinosa-mediated reduction and Rhodococcus rhodochrous-mediated oxidation was further examined.Keywords
This publication has 93 references indexed in Scilit:
- A short synthesis of (−)-(4R,5S)-sitophilure using the regio- and stereoselective reduction of 3-acyltetrahydrothiopyran-4-ones with baker's yeastTetrahedron Letters, 1992
- Enantioselective reduction of 4-oxo-3-tetrahydrothiopyranyl-acetates with bakers' yeast and application to the synthesis of a prostaglandin intermediate in optically pure formTetrahedron Letters, 1991
- Highly enantio- and diastereoselective reduction of sulfur-functionalized cyclic ketones with baker's yeastTetrahedron Letters, 1991
- The substrate- and stereoselectivity of microbial reductions of 1,4-dithiaspiro[4.5]decanones and 1,5-dithiaspiro[5.5]undecanonesCanadian Journal of Chemistry, 1990
- 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’ YeastBulletin of the Chemical Society of Japan, 1989
- Preparation of chiral C5-building blocks for terpene synthesis by bakers' yeast reduction of sulfur-functionalized prenyl derivativesTetrahedron Letters, 1988
- A General Method for the Synthesis of Both Enantiomers of Optically Pure β-Hydroxy Esters from (S)-(p-Chlorophenylsulfinyl)acetone Easily Obtainable by Kinetic Resolution with Bakers’ YeastBulletin of the Chemical Society of Japan, 1988
- Optically pure (s)-3-phenylthio-1,2-propanediol: synthesis by the yeast reduction and use as a precursor of both enantiomers of secondary alcoholsTetrahedron Letters, 1985
- A synthesis of (S,S)-(+)-grahamimycin A1Tetrahedron Letters, 1983
- Asymmetric reduction of carbonyl compounds by yeast. IV. Preparation of optically active β-hydroxy sulfides, sulfoxides and sulfonesAustralian Journal of Chemistry, 1978