Cyclopropane–alkene metathesis by gold(i)-catalyzed decarbenation of persistent cyclopropanes

Abstract

A gold(I)-catalyzed cyclopropane–alkene metathesis has been demonstrated with two new families of cyclopropane derivatives of naphthalene and phenanthrene (benzo-fused norcaradienes). In this process, metal carbene units are transferred from a persistent cyclopropane to an alkene, upon release of naphthalene or phenanthrene, allowing the diastereoselective synthesis of a wide range of aryl and vinyl cyclopropanes.