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
Publication statusPublished - 1999

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sulfoxide
2-Propanol
Yeast
Stereoselectivity
Stereochemistry
Protonation
Acetone
Sulfur
Isomers
Carbon
Atoms
Substrates

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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. / Sakai, Atsushi; Bakke, Mikio; Ohta, Hiromichi; Kosugi, Hiroshi; Sugai, Takeshi.

In: Chemistry Letters, No. 11, 1999, p. 1255-1256.

Research output: Contribution to journalArticle

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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.",
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T1 - 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

AU - Sakai, Atsushi

AU - Bakke, Mikio

AU - Ohta, Hiromichi

AU - Kosugi, Hiroshi

AU - Sugai, Takeshi

PY - 1999

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N2 - (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.

AB - (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.

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