Desymmetrization of cis-1,2-dihydroxycycloalkanes by stereoselective lipase mediated esterification

Meso-compounds 1,2-dihydroxycyclopentane (1), 1,2-dihydroxycyclohexane (2) and 1,2-dyhydroxycycloheptane (3) were desymmetrised by enantiotoposelective esterification with vinyl acetate in tert-butyl methyl ether catalysed by lipases from Pseudomonas cepacia, Candida antarctica (Novozym 435®) and Mucor miehei (Lipozyme TM®). 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.