A new approach to substituted cyclobutanes:: Direct β-deprotonation/magnesiation of cyclobutane carboxamides

被引：18

作者：

Eaton, PE

Zhang, MX

Komiya, N

Yang, CG

Steele, I

Gilardi, R

机构：

[1] Univ Chicago, Dept Chem, Chicago, IL 60637 USA

[2] USN, Res Lab, Struct Matter Lab, Washington, DC 20375 USA

来源：

SYNLETT | 2003年 / 09期

关键词：

metalation; diastereoselective; amido-Grignards; cyclobutanes; substituent effects;

D O I：

10.1055/s-2003-40331

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

BuMoN(i-Pr)(2) is shown to be kinetically and thermodynandcally efficient for deprotonation/magnesiation cis and beta to an activating carboxamido group on a cyclobutane ring. The resulting carboxamido-stabilized amido-Grignards are useful reagents. The method provides an entirely new approach to controlled substitution on cyclobutanes. BuMaN(i-Pr)(2) will also metalate pivaloyl amides.

引用

页码：1275 / 1278

页数：4

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