Kinetic resolution of fluorinated propargyl alcohols by lipase-catalyzed enantioselective transesterification

Sung Jin Ko, Jung Yun Lim, Nan Young Jeon, Keehoon Won, Deok Chan Ha, Bum Tae Kim, Hyuk Lee

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

In order to obtain optically active fluorinated propargyl alcohols, a lipase-catalyzed kinetic resolution has been carried out. The effect of lipase types, organic solvents, reaction temperature, and acyl donors was examined in the lipase-catalyzed transesterification of 1,1,1-trifluoro-4-phenyl-3-butyn-2-ol. Various enantiomerically pure fluorinated propargyl alcohols have been successfully prepared in good enantiomeric excess (>84%) by Novozym 435-catalyzed transesterification with vinyl butanoate at 60 °C in n-hexane. In some cases, the enantiomeric purities were excellent (>99% ee).

Original languageEnglish
Pages (from-to)1109-1114
Number of pages6
JournalTetrahedron Asymmetry
Volume20
Issue number10
DOIs
Publication statusPublished - 2009 Jun 5

ASJC Scopus subject areas

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

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