Rhodium-catalyzed asymmetric 1, 4-addition of arylboron reagents to α, β-unsaturated esters

…, T Senda, H Kurushima, M Ogasawara, T Hayashi

Index: Takaya, Yoshiaki; Senda, Taichi; Kurushima, Hiroaki; Ogasawara, Masamichi; Hayashi, Tamio Tetrahedron Asymmetry, 1999 , vol. 10, # 20 p. 4047 - 4056

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Citation Number: 154

Abstract

Reaction of arylboron reagents, arylboronic acids or arylborates, which are readily accessible by lithiation of aryl bromides followed by treatment with trimethoxyborane, with α, β-unsaturated esters in the presence of rhodium/(S)-binap catalyst proceeded with high enantioselectivity to give high yields of optically active β-aryl esters of up to 98% ee. The enantioselectivity depends on the steric bulkiness of the ester moiety.