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

Abstract

[reaction: see text] A copper-catalyzed asymmetric addition of diorganozinc reagents to N-phosphinoylimines has been developed for the synthesis of chiral alpha,alpha,alpha-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).