TY - JOUR
T1 - The effect of temperature on the lipase-catalyzed asymmetric protonation of 1-acetoxy-2-methylcyclohexene giving (R)-2-methylcyclohexanone
AU - Sakai, Takashi
AU - Matsuda, Akiko
AU - Tanaka, Yuko
AU - Korenaga, Toshinobu
AU - Ema, Tadashi
N1 - Funding Information:
This work was supported by a Grant-in-Aid for Scientific Research from the Ministry of Education, Culture, Sports, Science and Technology of Japan.
PY - 2004/6/21
Y1 - 2004/6/21
N2 - Lipase-catalyzed enantioface-selective protonation of the enol acetate of 2-methylcyclohexanone was performed by using Burkholderia cepacia lipase immobilized on porous ceramic particles, 'Lipase PS-C II' (Amano Enzyme Inc.), in i-Pr2O and ethanol, giving (R)-2-methylcyclohexanone with 77% ee at best with 82% conversion at 0°C. The enantioselectivity (E-value) was found to be temperature dependent and significant in controlling the efficiency of the asymmetric protonation.
AB - Lipase-catalyzed enantioface-selective protonation of the enol acetate of 2-methylcyclohexanone was performed by using Burkholderia cepacia lipase immobilized on porous ceramic particles, 'Lipase PS-C II' (Amano Enzyme Inc.), in i-Pr2O and ethanol, giving (R)-2-methylcyclohexanone with 77% ee at best with 82% conversion at 0°C. The enantioselectivity (E-value) was found to be temperature dependent and significant in controlling the efficiency of the asymmetric protonation.
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U2 - 10.1016/j.tetasy.2004.05.008
DO - 10.1016/j.tetasy.2004.05.008
M3 - Article
AN - SCOPUS:2942652790
SN - 0957-4166
VL - 15
SP - 1929
EP - 1932
JO - Tetrahedron Asymmetry
JF - Tetrahedron Asymmetry
IS - 12
ER -