Copper-Catalyzed Three-Component Carboiminolactonization of Electron-Deficient Olefins

Herein we report the three-component copper-catalyzed
carboiminolactonization
of α,β-unsaturated carbonyl derivatives. In the presence
of a Cu(I) catalyst, α-haloesters, electron-deficient alkenes,
and primary amines couple to generate γ-iminolactones in a single
step. The scope of the reaction is explored with respect to the three
coupling partners. Nineteen examples are presented with yields of
these hydrolytically labile heterocycles of up to 69%. Mechanistic
investigations support the formation of an oxocarbenium by way of
an atom transfer radical addition (ATRA) intermediate.