Copper-Catalyzed Borylative Cross-Coupling of Allenes and Imines: Selective Three-Component Assembly of Branched Homoallyl Amines

Abstract

A copper-catalyzed three-component coupling of allenes, bis(pinacolato)diboron, and imines allows regio-, chemo-, and diastereoselective assembly of branched α,β-substituted-γ-boryl homoallylic amines, that is, products bearing versatile amino, alkenyl, and borane functionality. Alternatively, convenient oxidative workup allows access to α-substituted-β-amino ketones. A computational study has been used to probe the stereochemical course of the cross-coupling.

Keywords: allenes; boron; copper; cross-coupling; imines.