Novozyme 435 Asymmetric Hydrolysis of Enol Ester with Series Acid Moiety

作者：Li Quan; Jia Weimin^*; Wang Zhijian; Guo Xiaodan

来源：Asian Journal of Chemistry, 2014, 26(2): 607-610.

DOI：10.14233/ajchem.2014.16200

• Asymmetric hydrolysis
• Specific rotation
• Enol ester
• (R)-2-Pentylcyclopentanone
• Chiral acid moiety

(R)-2-pentylcyclopentanone can be synthesigd by the asymmetric hydrolysis of enol esters, catalyzed by immobilized candida antarctica (novozyme 435) lipas. Different acid moieties influence the stereoselectivity of lipase. Enol esters can be prepared from anhydrides and 2-pentylcyclopentanone. When introducing optical (S)-(+)-2-methyl-butyric acid, the hydrolysis of optical enol ester showed great enhancement of the specific rotation compared to the racemic emol ester, the specific rotation of product raise from [alpha](D)(25)-10 degrees (c 0.1, CH3OH) to [alpha](D)(25)-72 degrees (c 0.1, CH3OH). However, when bringing chiral acid moity, the specific rotation still can not catch up with the value compared to the isobutyric moiety. the specific rotation of (R)-2-pentylcyclopentanone is [alpha](D)(25)-102.20 degrees (c 0.1, CH3OH), the optimum temperature and pH were 30 degrees C and 6.5, respectively. Then 81.06% ee of (R)-delta-decalactone was prepared by the Baeyer-Villiger oxidation of (R)-2-pentylcyclopentanone.

• 出版日期2014-1
• 单位上海应用技术大学