T. Kometani et al., ENZYMATIC RESOLUTION OF 2-FLUORO-2-ARYLACETIC ACID-DERIVATIVES, Journal of molecular catalysis. B, Enzymatic, 5(1-4), 1998, pp. 171-174
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.
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