Diastereo- and Site-Selective Synthesis of Bishomoallyl Amines by Nickel-Catalyzed Multicomponent Couplings with Imines and Dienes Enabled by a Pyridyl-Phosphine Ligand

A catalytic multicomponent coupling method for the site-selective and diastereoselective preparation of secondary amines containing tertiary and quaternary carbon centers is disclosed. Reactions employ simple reagents (imines, 1,3-dienes, and organoborons) and are promoted by a readily available nickel-catalyst supported by a pyridyl-phosphine ligand. The influence of diene substitution is shown to be a key factor in controlling the selectivity between quaternary and tertiary carbon center formation.