(S)-β,ω-Dihydroxyalkyl Phenyl Sulfones. Synthesis by Bakers Yeast Reduction and Use as Precursors of Optically Active Lactones
- 5 September 1988
- journal article
- research article
- Published by Oxford University Press (OUP) in Chemistry Letters
- Vol. 17 (9) , 1537-1540
- https://doi.org/10.1246/cl.1988.1537
Abstract
The enantioselective reduction of ω-hydroxy-β-ketoalkyl phenyl sulfones with bakers’ yeast gives (S)-ω,β-dihydroxyalkyl phenyl sulfones, which are convenient precursors for optically active lactones as shown in the synthesis of (R)-4-hexanolide and (R)-umbelactone.Keywords
This publication has 21 references indexed in Scilit:
- Preparation of chiral C5-building blocks for terpene synthesis by bakers' yeast reduction of sulfur-functionalized prenyl derivativesTetrahedron Letters, 1988
- Chemistry of baker's yeast reduction products: Use of optically active (S)-(+)-1-(p-toluenesulfonyl)propan-2-ol and (S)-(+)-1-(phenylsulfonyl)propan-2-ol in synthesis.Tetrahedron Letters, 1986
- Asymmetric reduction with baker's yeast.Journal of Synthetic Organic Chemistry, Japan, 1986
- 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
- Diastereo- and enantioselective reduction of α,β-diketodithiane with the baker's yeastTetrahedron Letters, 1985
- Enantiospecific synthesis of optically pure (3s)-hydroxy esters by the stereocontrolled yeast reduction of α-sulfenyl-β-ketoestersTetrahedron Letters, 1984
- Microbial Asymmetric Catalysis—Enantioselective Reduction of Ketones [New Synthetic Methods (45)]Angewandte Chemie International Edition in English, 1984
- Stereochemical control in yeast reductionTetrahedron Letters, 1984
- Asymmetric reduction of carbonyl compounds by yeast. IV. Preparation of optically active β-hydroxy sulfides, sulfoxides and sulfonesAustralian Journal of Chemistry, 1978
- Recent developments in sulfone chemistryTetrahedron, 1977