Candida antarctica lipase B-mediated regioselective acylation of dihydroxybenzenes in organic solvents

Abstract

Candida antarctica lipase B proved to be a highly active biocatalyst for the direct acylation of phenolic hydroxy groups of substituted hydroquinones and resorcinols, which have rarely been reported so far. More importantly, the acylation reactions took place generally in a markedly regioselective manner: the hydroxy group remote from the substituent was preferentially acylated. In the case of substituted hydroquinones, the selectivity increased with the increase in the bulk of the substituent. Interestingly, the 1-O-monoacylated derivatives were obtained as the sole products in the case of 4-substituted resorcinols.