Selective Diethylzinc Reduction of Imines in the Presence of Ketones Catalyzed by Ni(acac)₂

Abstract

A selective reduction method of an electronically deficient imine in the presence of ketone was developed by employing Et2Zn and 5 mol % of Ni(acac)2. The method was applied in the reduction of SS-tert-butanesulfinyl ketimines 1 to afford amines 2 in 23−92% yields and 73:27 to 98:2 diastereoselectivities. A plausible mechanism was proposed on the basis of an NMR study