Diastereoselective synthesis of 1,3-diamines by a domino reaction of imines, enamines, and trichlorosilane

Abstract

In this study, we report a new highly diastereoselective domino reaction of imines, enamines, and trichlorosilane. The reaction involves CC bond formation between the imine and enamine followed by the intramolecular reduction of the resulting iminium intermediate by the hydrosilyl group, affording a 1,2-anti-2,3-anti-1,3-diamine in good yield with high diastereoselectivity. Lewis base catalysts such as HMPA increased the chemical yield without decreasing the diastereoselectivity.