Functionalized 4-Carboxy- and 4-Keto-2,3-dihydropyrroles via Ni(II)-Catalyzed Nucleophilic Amine Ring-Opening Cyclizations of Cyclopropanes

Abstract

A general synthetic approach to vinylogous 4-carboxy- and 4-keto-2,3-dihydropyrroles is reported using Ni(ClO4)2·6H2O as a Lewis acid catalyst for nucleophilic amine ring-opening cyclizations of donor–acceptor (D–A) cyclopropanes. This methodology provided good to excellent yields of functionalized 2,3-dihydropyrroles under milder reaction conditions than previously reported and is amenable to a variety of D–A cyclopropanes and primary amines.