Tetrahedron letters

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

S Tominaga, Y Oi, T Kato, DK An, S Okamoto

Index: Tominaga, Satoshi; Oi, Yukinao; Kato, Toshio; An, Duk Keun; Okamoto, Sentaro Tetrahedron Letters, 2004 , vol. 45, # 29 p. 5585 - 5588

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Citation Number: 113

Abstract

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.