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

In this study, we report a new highly diastereoselective domino reaction of imines, enamines, and trichlorosilane. The reaction involves C C 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. (c) 2014 Elsevier Ltd. All rights reserved.