DESYMMETRIZATION OF CIS-1,2-DIHYDROXYCYCLOALKANES BY STEREOSELECTIVE LIPASE-MEDIATED ESTERIFICATION

Meso-compounds 1,2-dihydroxycyclopentane (1), 1,2-dihydroxycyclohexane (2) and 1,2-dihydroxycycloheptane (3) were desymmetrised by enantiotoposelective esterification with vinyl acetate in tert-butyl methyl ether catalysed by lipases from Pseudomonas cepacia, Candida antarctica (Novozym 435(R)) and Mucor miehei (Lipozyme TM(R)). Both of the lipases from P. cepacia and M. miehei afforded the (1S,2R)-acetate (+)-1a and (1R,2S)-acetates (-)-2a and (+)-3a in good enantiomeric excesses and chemical yield.