Tetrahedron p. 6017 - 6028 (1994)
Update date:2022-08-04
Topics:
Yanagisawa, Akira
Nomura, Nobuyoshi
Yamamoto, Hisashi
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 without losing the double bond geometry.
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