Copper-Catalyzed Enantioselective Addition of Styrene-Derived Nucleophiles to Imines Enabled by Ligand-Controlled Chemoselective Hydrocupration

The copper-catalyzed
intermolecular enantioselective addition of
styrenes to imines has been achieved under mild conditions at ambient
temperature. This process features the use of styrenes as latent carbanion
equivalents via the intermediacy of catalytically generated benzylcopper
derivatives, providing an effective means for accessing highly enantiomerically
enriched amines bearing contiguous stereocenters. Mechanistic studies
shed light on the origin of the preferential styrene hydrocupration
in the presence of an imine with the Ph-BPE-derived copper catalyst.