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

doi:10.1016/j.tetasy.2009.03.041

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

College of Science

Research output: Contribution to journal › Article › peer-review

9 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 language	English
Pages (from-to)	1109-1114
Number of pages	6
Journal	Tetrahedron Asymmetry
Volume	20
Issue number	10
DOIs	https://doi.org/10.1016/j.tetasy.2009.03.041
Publication status	Published - 2009 Jun 5

Bibliographical note

Funding Information:
This work was supported by grants from the Ministry of Knowledge Economy (Grant No. SI-0901) of the Republic of Korea and the Korea Research Council for Industrial Science and Technology (SK-0603).

ASJC Scopus subject areas

Catalysis
Physical and Theoretical Chemistry
Organic Chemistry
Inorganic Chemistry

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10.1016/j.tetasy.2009.03.041

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title = "Kinetic resolution of fluorinated propargyl alcohols by lipase-catalyzed enantioselective transesterification",

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).",

author = "Ko, {Sung Jin} and Lim, {Jung Yun} and Jeon, {Nan Young} and Keehoon Won and Ha, {Deok Chan} and Kim, {Bum Tae} and Hyuk Lee",

note = "Funding Information: This work was supported by grants from the Ministry of Knowledge Economy (Grant No. SI-0901) of the Republic of Korea and the Korea Research Council for Industrial Science and Technology (SK-0603).",

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doi = "10.1016/j.tetasy.2009.03.041",

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AU - Ko, Sung Jin

AU - Lim, Jung Yun

AU - Jeon, Nan Young

AU - Won, Keehoon

AU - Ha, Deok Chan

AU - Kim, Bum Tae

AU - Lee, Hyuk

N1 - Funding Information: This work was supported by grants from the Ministry of Knowledge Economy (Grant No. SI-0901) of the Republic of Korea and the Korea Research Council for Industrial Science and Technology (SK-0603).

PY - 2009/6/5

Y1 - 2009/6/5

N2 - 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).

AB - 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).

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

Abstract

Bibliographical note

ASJC Scopus subject areas

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