Catalytic enantioselective synthesis of azacycloalkenes via intermolecular rhodium carbenoid C–H insertion/ring-closing metathesis sequence

Abstract

Enantiomerically enriched cyclopropanes and products of C–H insertion reactions were obtained in excellent combined yields and enantioselectivities as a consequence of rhodium-catalyzed decomposition of vinyl diazoacetate in the presence of tert-butoxycarbonyl-(Boc)-protected amines as trapping agents. A series of enantiomerically enriched six- to eight-membered nitrogen-containing heterocycles were subsequently prepared via ring-closing metathesis of the dienes catalyzed by ruthenium benzylidene complex.