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 SN2′ reaction pathway to give γ-substituted product in excellent yield. The method was applied to asymmetric reaction by using optically active NHC ligands.
[Yanagisawa, Akira; Hibino, Hiroaki; Nomura, Nobuyoshi; Yamamoto, Hisashi Journal of the American Chemical Society, 1993 , vol. 115, # 13 p. 5879 - 5880]