The effect of temperature on the lipase-catalyzed asymmetric protonation of 1-acetoxy-2-methylcyclohexene giving (R)-2-methylcyclohexanone

Takashi Sakai, Akiko Matsuda, Yuko Tanaka, Toshinobu Korenaga, Tadashi Ema

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

Lipase-catalyzed enantioface-selective protonation of the enol acetate of 2-methylcyclohexanone was performed by using Burkholderia cepacia lipase immobilized on porous ceramic particles, 'Lipase PS-C II' (Amano Enzyme Inc.), in i-Pr2O and ethanol, giving (R)-2-methylcyclohexanone with 77% ee at best with 82% conversion at 0°C. The enantioselectivity (E-value) was found to be temperature dependent and significant in controlling the efficiency of the asymmetric protonation.

Original languageEnglish
Pages (from-to)1929-1932
Number of pages4
JournalTetrahedron Asymmetry
Volume15
Issue number12
DOIs
Publication statusPublished - Jun 21 2004

ASJC Scopus subject areas

  • Catalysis
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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