No 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.

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.

Copper-catalyzed coupling of readily available ketiminoesters, allenes and a diboron affords densely functionalized quaternary α-amino esters bearing adjacent stereocenters and versatile vinyl boronate motifs. The method utilizes a commercially available copper(I) catalyst, operates at ambient temperature and features a catalytic allyl cupration of ketiminoesters.

We explore the breadth of the copper catalysed functionalisation of allenes, which enables efficient access to enantioenriched, densely functionalised molecules.