Facile generation of α-silyl carbanion of trimethylsilyl group assisted by intramolecular pyridyl group coordination

被引：31

作者：

Itami, K ^{[1
]}

Mitsudo, K ^{[1
]}

Yoshida, J ^{[1
]}

机构：

[1] Kyoto Univ, Dept Synthet Chem & Biol Chem, Kyoto 6068501, Japan

来源：

TETRAHEDRON LETTERS | 1999年 / 40卷 / 30期

关键词：

D O I：

10.1016/S0040-4039(99)01027-8

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Novel methodology for the generation of alpha-silyl carbanion by the deprotonation of trimethylsilyl group with tert-butyllithium or LDA has been developed. This newly developed alpha-lithiation protocol is based on the intramolecular pyridyl group coordination to stabilize the alpha-silyl carbanion, together with the inherent silicon alpha effect. The importance of the use of the 2-pyridyl group in 'pyridyl'- and 'silyl'-directed alpha-lithiation has been confirmed by the control experiments utilizing phenyltrimethylsilane and (3-pyridyl)trimethylsilane. (C) 1999 Elsevier Science Ltd. All rights reserved.

引用

页码：5533 / 5536

页数：4

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