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

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

Research output: Contribution to journalArticle

6 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

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Enzyme kinetics
Transesterification
Lipases
Lipase
alcohols
Alcohols
Kinetics
kinetics
purity
Hexane
Organic solvents
temperature
propargyl alcohol
Temperature

ASJC Scopus subject areas

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

Cite this

Kinetic resolution of fluorinated propargyl alcohols by lipase-catalyzed enantioselective transesterification. / Ko, Sung J.; Lim, Jung Yun; Jeon, Nan Young; Won, Keehoon; Ha, Deok-Chan; Kim, Bum Tae; Lee, Hyuk.

In: Tetrahedron Asymmetry, Vol. 20, No. 10, 05.06.2009, p. 1109-1114.

Research output: Contribution to journalArticle

Ko, Sung J. ; Lim, Jung Yun ; Jeon, Nan Young ; Won, Keehoon ; Ha, Deok-Chan ; Kim, Bum Tae ; Lee, Hyuk. / Kinetic resolution of fluorinated propargyl alcohols by lipase-catalyzed enantioselective transesterification. In: Tetrahedron Asymmetry. 2009 ; Vol. 20, No. 10. pp. 1109-1114.
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