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

作者：Kashiwagi Takeru; Kotani Shunsuke; Nakajima Makoto^*; Sugiura Masaharu

来源：Tetrahedron Letters, 2014, 55(11): 1924-1926.

DOI：10.1016/j.tetlet.2014.01.152

• 1,3-Diamines
• Domino reaction
• Enamine
• Lewis base catalyst
• 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.

• 出版日期2014-3-12