Tetrahedron

Transition metal-catalyzed substitution reaction of allylic phosphates with Grignard reagents

A Yanagisawa, N Nomura, H Yamamoto

Index: Yanagisawa, Akira; Nomura, Nobuyoshi; Yamamoto, Hisashi Tetrahedron, 1994 , vol. 50, # 20 p. 6017 - 6028

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Citation Number: 89

Abstract

SN2-selective Grignard coupling with primary allylic diphenylphosphates was successfully achieved using Ni or Fe catalyst. In sharp contrast, a catalytic amount of CuCN· 2LiCl promoted a SN2′-selective coupling reaction. In the presence of the copper catalyst, stereochemically homogeneous γ-disubstituted allyl Grignard reagents reacted at the less substituted allylic terminus (α-position) with an allylic diphenylphosphate selectively ...