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 | |
| Publication status | Published - 2009 Jun 5 |
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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 journal › Article
}
TY - JOUR
T1 - Kinetic resolution of fluorinated propargyl alcohols by lipase-catalyzed enantioselective transesterification
AU - Ko, Sung J.
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 - http://www.scopus.com/inward/record.url?scp=66549106244&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=66549106244&partnerID=8YFLogxK
U2 - 10.1016/j.tetasy.2009.03.041
DO - 10.1016/j.tetasy.2009.03.041
M3 - Article
AN - SCOPUS:66549106244
VL - 20
SP - 1109
EP - 1114
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
SN - 0957-4166
IS - 10
ER -