; AJC-14597 (R)-2-pentylcyclopentanone can be synthesized by the asymmetric hydrolysis of enol esters, catalyzed by immobilized candida antarctica (novozyme 435) lipase. 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 enol ester, the specific rotation of product raise from [α] 25 D-10° (c 0.1, CH3OH) to [α] 25 D-72° (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 [α] 25 D-102.20° (c 0.1, CH3OH), the optimum temperature and pH were 30 °C and 6.5, respectively. Then 81.06 % ee of (R)-δ-decalactone was prepared by the Baeyer-Villiger oxidation of (R)-2-pentylcyclopentanone.