Highly efficient biocatalytic desymmetrization of meso carbocyclic 1,3-dicarboxamides: a versatile route for enantiopure 1,3-disubstituted cyclohexanes and cyclopentanes

Abstract

A versatile biocatalytic desymmetric strategy for efficiently accessing enantiopure 1,3-disubstituted cyclohexanes and cyclopentanes was developed. Desymmetric hydrolysis of a series of meso carbocyclic 1,3-dicarboxamides catalyzed by Rhodococcus erythropolis AJ270 whole cells under mild conditions afforded 3-carbamoylcyclic carboxylic acid derivatives in 81–95% yields and >99.5% ee values. The desymmetrization of different types of substrates shows a general S-selectivity, and the catalytic efficiency and enantioselectivity show dependence on the cyclic structure of the substrates. The biocatalytic products were conveniently transformed to chiral bicyclic oxazolidinone compounds.