Synthesis of 4-iodo-3-furanones utilizing electrophile-induced tandem cyclization/1,2-migration reactions

被引：114

作者：

Crone, Benedikt ^{[1
]}

Kirsch, Stefan F. ^{[1
]}

机构：

[1] Tech Univ Munich, Dept Chem, D-85747 Garching, Germany

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 14期

关键词：

D O I：

10.1021/jo070695n

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two protocols for the construction of 4-iodo-3-furanones through a sequence consisting of cyclization and 1,2-migration of 2-alkynyl-2-silyloxy carbonyl compounds were developed. In one, electrophilic cyclization is directly induced by N-iodosuccinimide (NIS). In the second less limited variant, AuCl3 catalyzes the tandem reaction in the presence of NIS to provide highly substituted heterocycles in moderate to excellent yields.

引用

页码：5435 / 5438

页数：4

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