Selenium-catalyzed halolactonization: Nucleophilic activation of electrophilic halogenating reagents

被引：90

作者：

Mellegaard, SR ^{[1
]}

Tunge, JA ^{[1
]}

机构：

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

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 25期

关键词：

D O I：

10.1021/jo048460o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Diphenyl diselenide catalyzes the halolactonization of unsaturated acids with N-halosuccinimides under mild conditions. The diselenide not only accelerates the reactions, but in some cases affords regiocontrol in favor of gamma-lactone products. Experiments show that the regioselectivity in favor of gamma-lactones is a result of kinetic rather than thermodynamic control.

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页码：8979 / 8981

页数：3

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