Efficient synthesis of highly enantiopure β-lactam derivatives from biocatalytic transformations of amides and nitriles

Abstract

Catalyzed by Rhodococcus erythropolis AJ270, a nitrile hydratase and amidase containing microbial strain, under mild conditions, kinetic resolution of racemic amides provides an efficient and scalable route to highly enantioenriched R-4-carboxymethyl-β-lactams and S-4-carbamoylmethyl-β-lactams despite the substrates contain a stereogenic center that is β-positioned to amide functionality. Synthetic potential of the method was demonstrated by the constructions of novel β-lactam-fused heterocyclic compounds through convenient and practical chemical transformations.