LIPASE-CATALYZED KINETIC RESOLUTION OF A SERIES OF ESTERS HAVING A SULFOXIDE GROUP AS THE STEREOGENIC CENTER

A series of methyl 2-(alkylsulfinyl)benzoates (alkyl = C1, n-C4, n-C-8, n-C-12 and n-C-16) was investigated with respect to substrate behaviour and enantioselectivity in a lipase (Candida rugosa)-catalyzed hydrolytic reaction. Although three bonds separate the stereogenic centre and the ester carbonyl group, very high enantioselectivity values (>100) could be obtained. It was found that the enzyme consistently showed a strong kinetic preference for the (-)-(S)-enantiomer.