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Kinetic resolution of fluorinated propargyl alcohols by lipase-catalyzed enantioselective transesterification
- Authors
- Ko, Sung-Jin; Lim, Jung Yun; Jeon, Nan Young; Won, Keehoon; Ha, Deok-Chan; Kim, Bum Tae; Lee, Hyuk
- Issue Date
- 5-Jun-2009
- Publisher
- PERGAMON-ELSEVIER SCIENCE LTD
- Keywords
- kinetic resolution; fluorinated propargyl alcohols; lipase; enantioselective
- Citation
- TETRAHEDRON-ASYMMETRY, v.20, no.10, pp.1109 - 1114
- Indexed
- SCIE
SCOPUS
- Journal Title
- TETRAHEDRON-ASYMMETRY
- Volume
- 20
- Number
- 10
- Start Page
- 1109
- End Page
- 1114
- ISSN
- 0957-4166
- 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 degrees C in n-hexane. In some cases, the enantiomeric purities were excellent (>99% ee). (C) 2009 Elsevier Ltd. All rights reserved.
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