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14 Sep 13:00

Enantioselective Generation of Adjacent Stereocenters in a Copper-Catalyzed Three-Component Coupling of Imines, Allenes, and Diboranes

by Kay Yeung, Rebecca E. Ruscoe, James Rae, Alexander P. Pulis, David J. Procter

Abstract

A highly enantio- and diastereoselective copper-catalyzed three-component coupling affords the first general synthesis of homoallylic amines bearing adjacent stereocenters from achiral starting materials. The method utilizes a commercially available NHC ligand and copper source, operates at ambient temperature, couples readily available simple imines, allenes, and diboranes, and yields high-value homoallylic amines that exhibit versatile amino, alkenyl, and boryl units.

Thumbnail image of graphical abstract

A copper-catalyzed three-component coupling affords homoallylic amines with adjacent stereocenters from achiral starting materials with high enantio- and diastereoselectivity. The method utilizes a commercially available NHC ligand and copper source, operates at ambient temperature, couples simple imines, allenes, and diboranes, and yields valuable homoallylic amines with versatile amino, alkenyl, and boryl units.