Synthesis of 2, 5-disubstituted pyrrolidines from N-alkenyl and alkynyl N-Benzoyloxysulfonamides catalyzed by (CuOTf)2 · C 6H6

Abstract

A new synthetic method of 2, 5-disubstituted pyrrolidines is developed by the cyclization of unsaturated N-benzoyl- oxysulfonamides by (CuOTf) 2-C6H6; in refluxing dichloroethane. Various N-A- and N-5-alkenyl and alkynyl N-benzoyl- oxysulfonamides are cyclized to give pyrrolidines. The cyclization proceeds via addition of sulfonamidoyl radicals to intramolecular unsaturated bonds or allylic hydrogen abstraction with the radical intermediates.