Mechanistic studies on selectivity in the B(C6F5)3-catalyzed allylstannation of aldehydes:: Is hypercoordination at boron responsible?

被引：71

作者：

Blackwell, JM ^{[1
]}

Piers, WE ^{[1
]}

Parvez, M ^{[1
]}

机构：

[1] Univ Calgary, Dept Chem, Calgary, AB T2N 1N4, Canada

来源：

ORGANIC LETTERS | 2000年 / 2卷 / 05期

关键词：

D O I：

10.1021/ol0000105

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The selective, B(C6F5)(3)-catalyzed allylstannation of aldehydes with proximal donor groups is shown to proceed via borane abstraction of the allyl group from the tin reagent and activation of the substrate by "Bu3Sn+ ", This is supported by a number of F-19 NMR experiments. The selectivity of the reaction is not attributable to hypercoordinate boron as proposed by the discoverers of this highly selective reaction but likely involves chelation at tin.

引用

页码：695 / 698

页数：4

共 27 条

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