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

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

doi:10.1016/j.tetasy.2009.03.041

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

Ko, Sung-Jin;
Lim, Jung Yun;
Jeon, Nan Young;
Won, Keehoon;
Ha, Deok-Chan;
외 2명

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10

초록

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.

키워드

kinetic resolution; fluorinated propargyl alcohols; lipase; enantioselective; CANDIDA-ANTARCTICA; ALLYLIC ALCOHOLS; PURE; REDUCTION; ACYLATION

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

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

DOI: 10.1016/j.tetasy.2009.03.041

발행일: 2009-06-05

유형: Article

저널명: Tetrahedron Asymmetry

권: 20

호: 10

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