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

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 yi...

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Bibliographic Details
Published in:Tetrahedron: asymmetry 1999-10, Vol.10 (20), p.4047-4056
Main Authors: Takaya, Yoshiaki, Senda, Taichi, Kurushima, Hiroaki, Ogasawara, Masamichi, Hayashi, Tamio
Format: Article
Language:English
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Summary: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.
ISSN:0957-4166
1362-511X
DOI:10.1016/S0957-4166(99)00417-6