Regio- and enantioselective formation of tetrazole-bearing quaternary stereocenters via palladium-catalyzed allylic amination

Abstract

Based on palladium-catalyzed allylic amination reaction, the first general example of enantioselective formation of a tetrazole-bearing quaternary stereocenter has been developed. The protocol uses ambivalent tetrazole and vinyl cyclic carbonates as easily available coupling partners. This operationally simple methodology is further characterized by its wide substrate scope, high enantioselectivity and excellent branched to linear regioselectivity, thus unlocking a new platform that permits the synthesis of elusive quaternary N²-allylic tetrazoles, even in the context of late-stage functionalization.