ASYMMETRIC CONJUGATE ADDITIONS TO CHIRAL BICYCLIC LACTAMS - A STEREOSELECTIVE, CONCISE SYNTHESIS OF CHIRAL 2-ALKYL-3,4-AZIRIDINOPYRROLIDINES

摘要

Stereoselective, conjugate additions of primary amines to chiral alpha-iodo alpha, beta- unsaturated bicyclic lactams are described. Typical yields of the resulting aziridinolactams ranged from 60-90% with facial diastereoselectivities of >98:2 in all cases. Selected optically pure aziridinobicyclic lactams were transformed, by reductive cleavage, into chiral 2-alkyl, 3, 4-aziridinopyrrolidines. [References: 15]