Nickel-catalyzed Asymmetric Propargylic Amination of Propargylic Carbonates with Aniline Derivatives

Abstract

A study for the development of the nickel-catalyzed highly enantioselective propargylic amination of propargylic carbonates with aniline derivatives is described. The reaction of internal alkyne-substituted propargylic carbonates with a series of aniline derivatives smoothly proceeded in DMSO using a combination of Ni(cod)2 and (R)-SEGPHOS as the catalyst to give the corresponding chiral propargylic amines in 61–93% yields with 91–97% ee (24 examples).