Catalytic Asymmetric Synthesis of α,α,α-Trifluoromethylamines by the Copper-Catalyzed Nucleophilic Addition of Diorganozinc Reagents to Imines

A copper-catalyzed asymmetric addition of diorganozinc reagents to N-phosphinoylimines has been developed for the synthesis of chiral α,α,α-trifluoromethylamines. The trifluoromethyl ketimines, generated in situ from the corresponding hemiaminals, led to the chiral amides in high yields (71−89%) and excellent enantiocontrol (91−99% ee).