Nitrile and Amide Biotransformations for the Synthesis of Enantiomerically Pure 3-Arylaziridine-2-carboxamide Derivatives and Their Stereospecific Ring-Opening Reactions

摘要

Catalyzed by Rhodococcus erythropolis AJ270 (whole cell catalyst) under very mild conditions, a number of racemic trans-3-arylaziridine-2-carbonitriles and amides were efficiently transformed into enantiopure 2R,3S-3-arylaziridme-2-carboxamides. While the nitrile hydratase exhibits low selectivity against nitrile substrates, the amidase is highly enantioselective toward 2R,3S-3-arylaziridine-2-carboxam-ides. Upon the treatment with catalytic hydrogenation, amine, or water in the presence of one equivalent of TFA, the resulting aziridine-2-carboxamides underwent highly efficient and stereospecific ring-opening reactions to produce enantiopure α-amino-, α,β-diamino-, and α-amino-β-hrydroxy-propanamide derivatives in high yields.