Copper-Catalyzed Three-Component 1,5-Carboamination of Vinylcyclopropanes
Andrei G. Popov, Vincent R. Viviani, Piotr Skumial, Theodore L. Jefferson, Samer G. Salman, Henry H. Baxter, Kami L. Hull
Abstract
The 1,5-copper-catalyzed carboamination of vinylcyclopropanes is presented. A carbon-centered radical, formed upon reduction of an alkyl halide by Cu(I), adds across the alkene of a vinylcyclopropane, triggering ring opening to generate a benzylic radical, which, finally, undergoes copper-mediated amination to afford a homoallylic amine. The reaction occurs with outstanding regio- and good to very good diastereoselectivities. The scope of the reaction is demonstrated with respect to all three components: alkyl halide, vinylcyclopropane, and amine nucleophile. A total of 38 examples are presented with an average yield of 60%.