γ-selective allylic substitution reaction with Grignard reagents catalyzed by copper N-heterocyclic carbene complexes and its application to enantioselective synthesis

The reaction of allylic compounds with alkyl Grignard reagents in the presence of a catalytic amount of copper N-heterocyclic carbene (NHC) complexes proceeded predominantly in an S(N)2' reaction pathway to give gamma-substituted product in excellent yield. The method was applied to asymmetric reaction by using optically active NHC ligands. (C) 2004 Elsevier Ltd. All rights reserved.