Regio and diastereoselective synthesis of allylic amine through hydrocupration of terminal alkynes

Abstract

Allylic amines play a crucial role in organic synthesis, owing to their versatility and unique chemical reactivity resulting from the allylic double bond. The significance of them is further evident in their incorporation as structural backbones in natural products and drug molecules. Allylic amines can be synthesized using various strategies including C-N bond formation via allylic substitution, C-H bond amination, and C-C bond formation by adding alkenyl metal to imine or reductive cross-coupling reactions. Herein, we develop an innovative approach to allylic amine synthesis based on copper-catalyzed stereoselective reductive cross-coupling between alkynes and α-Cl phthalimide. We demonstrate that the reaction is compatible with various functional groups under mild conditions. Interestingly, different from our proposed mechanism, the preliminary mechanistic study shows that the process does not involve the generation of a radical at the α-nitrogen position.