Synthesis of (Rc,Ss)-1,1,1-trifluoro-3-(p-molylsulfinyl)-2-propanol by an asymmetric reduction with a yeast, Yamadazyma farinosa, as a key-step

Atsushi Sakai, Mikio Bakke, Hiromichi Ohta, Hiroshi Kosugi, Takeshi Sugai

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

(Rc,Ss)-1,1,1-trifluoro-3-(p-tolysulfinyl)-2-propanol (>99% e.e.), an important reagent for the asymmetric protonation of substituted enolates, was prepared (70%) from (S)-methyl p-tolyl sulfoxide. The stereoselectivity of the Yamdazyma farinosa-catalyzed reduction of carbonyl groups, the key step for the introduction of an asymmetric carbon, was greatly affected by the stereochemistry of the asymmetric sulfur atom. The reduction of (S)-1,1,1-trifluoro-3-(p-tolylsulfinyl)-2-propanone proceeded smoothly and in a quite stereoselective manner to give the desired compound, while a 76 : 24 mixture of (Rc,Rs)-and (Sc,Rs)-isomers was obtained from the substrate with the opposite (R)-configuration.

Original languageEnglish
Pages (from-to)1255-1256
Number of pages2
JournalChemistry Letters
Issue number11
DOIs
Publication statusPublished - 1999 Jan 1

ASJC Scopus subject areas

  • Chemistry(all)

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