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

Department of Chemical and Biochemical Engineering

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

10 Scopus citations

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
State	Published - 5 Jun 2009

Access to Document

10.1016/j.tetasy.2009.03.041

Cite this

@article{8d7ed5f5b6ea4674bc14b85dddb0cd16,

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",

year = "2009",

month = jun,

day = "5",

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

language = "English",

volume = "20",

pages = "1109--1114",

journal = "Tetrahedron Asymmetry",

issn = "0957-4166",

publisher = "Elsevier Ltd",

number = "10",

}

TY - JOUR

T1 - Kinetic resolution of fluorinated propargyl alcohols by lipase-catalyzed enantioselective transesterification

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

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).

UR - https://www.scopus.com/pages/publications/66549106244

U2 - 10.1016/j.tetasy.2009.03.041

DO - 10.1016/j.tetasy.2009.03.041

M3 - Article

AN - SCOPUS:66549106244

SN - 0957-4166

VL - 20

SP - 1109

EP - 1114

JO - Tetrahedron Asymmetry

JF - Tetrahedron Asymmetry

IS - 10

ER -

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

Abstract

Access to Document

Other files and links

Fingerprint

Cite this