Cation-π control of regiochemistry of intramolecular Schmidt reactions en route to bridged bicyclic lactams

被引：85

作者：

Yao, Lei ^{[1
]}

Aube, Jeffrey ^{[1
]}

机构：

[1] Univ Kansas, Dept Med Chem, Lawrence, KS 66045 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2007年 / 129卷 / 10期

关键词：

D O I：

10.1021/ja068919r

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The regiochemistry of the intramolecular Schmidt reaction of 2-substituted ketones has proved susceptible to control by the placement of an aromatic group at an adjacent position, permitting the selective formation of a series of bridged bicyclic lactams from these substrates. This phenomenon is ascribed to the presence of stabilizing through-space interactions between the positively charged leaving group and the aromatic substituents in a key azidohydrin intermediate.

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页码：2766 / +

页数：3

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