Preparation of Sulfur-Containing Optically Active Secondary Alcohols Based on Pichia farinosa-Catalyzed anti-Prelog-Rule Reduction as the Key Step

Yoshikazu Ohtsuka, Osamu Katoh, Takeshi Sugai, Hiromichi Ohta

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33 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)483-491
Number of pages9
JournalBulletin of the Chemical Society of Japan
Volume70
Issue number2
Publication statusPublished - 1997 Feb

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Enantiomers
Sulfur
Alcohols
Ketones
Oxidation
Substrates
2-butanol
methylethyl ketone

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Preparation of Sulfur-Containing Optically Active Secondary Alcohols Based on Pichia farinosa-Catalyzed anti-Prelog-Rule Reduction as the Key Step. / Ohtsuka, Yoshikazu; Katoh, Osamu; Sugai, Takeshi; Ohta, Hiromichi.

In: Bulletin of the Chemical Society of Japan, Vol. 70, No. 2, 02.1997, p. 483-491.

Research output: Contribution to journalArticle

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