Lewis acid triggered N-alkylation of sulfoximines through nucleophilic ring-opening of donor–acceptor cyclopropanes: synthesis of γ-sulfoximino malonic diesters

Abstract

Scandium triflate (Sc(OTf)₃) catalyzed, mild, and regioselective ring-opening reaction of donor–acceptor (D–A) cyclopropanes has been developed using sulfoximines for the synthesis of γ-sulfoximino malonic diesters. This protocol allows the synthesis of different N-alkyl sulfoximines in good to excellent yields (up to 94%) with broad functional group tolerance. In this process, N–H and C–C bonds are cleaved to form new C–N and C–H bonds. The feasibility of this method is supported by a gram-scale reaction and synthetic elaboration of the obtained product.