ENZYMATIC RESOLUTION OF 2-FLUORO-2-ARYLACETIC ACID-DERIVATIVES

Optical resolutions of 2-fluoro-2-arylacetic acids, ArC FRCOOH (R = CN, H, and Me), were performed by enantioselective hydrolysis of the c orresponding esters using Candida rugosa lipase (CRL). The enantiosele ctivity of commercial CRL toward the esters was greatly improved when commercial CRL was treated with 2-propanol solution. In the enantiosel ective hydrolysis of these esters, as represented by ArC SMCOOR (S a nd M are small and medium substituents, respectively), the active site of the 2-propanol-treated CRL recognized fluorine as S in both PhCF(C H3)COOR and p-TolCF(CN)COOR but recognized fluorine as M in PhCHFCOOR. (C) 1998 Elsevier Science B.V. All rights reserved.