Copper(0)-induced aminocyclopropanation of olefins via deselenation of N,N-disubstituted aromatic selenoamides

Upon heating of a mixture of N,N-disubstituted aromatic selenoamides and several electron-deficient olefins in the presence of copper(0) powder, a novel deselenative cyclopropanation takes place to afford the corresponding aminocyclopropanes in good yields. When acrylonitrile is employed as an electron-deficient olefin, the aminocyclopentanation occurs in preference to the aminocyclopropanation by prolonging the reaction time. The obtained aminocyclopropane derivatives can be converted to the corresponding 1,4-dicarbonyl compounds upon treatment with 2 N HCl. (C) 2008 Elsevier Ltd. All rights reserved.