A Rhodium(II)-Catalyzed Formal [4+1]-Cycloaddition toward Spirooxindole Pyrrolone Construction Employing Vinyl Isocyanates as 1,4-Dipoles

被引：42

作者：

Meloche, Jennifer L. ^{[1
]}

Ashfeld, Brandon L. ^{[1
]}

机构：

[1] Univ Notre Dame, Dept Chem & Biochem, Notre Dame, IN 46556 USA

来源：

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2017年 / 56卷 / 23期

基金：

美国国家科学基金会;

关键词：

4+1]-cycloadditions; cyclopropane rearrangements; diazooxindoles; spirooxindole alkaloids; vinyl isocyanates; VINYLCYCLOPROPANE-CYCLOPENTENE REARRANGEMENT; ALDOSE REDUCTASE INHIBITORS; 4+1 ANNULATION REACTIONS; ELECTRON-RICH CARBENES; ORGANIC-SYNTHESIS; UNCARIA-TOMENTOSA; NATURAL-PRODUCTS; CYCLOPROPANATION/COPE REARRANGEMENT; ENANTIOSELECTIVE SYNTHESIS; NUCLEOPHILIC CARBENES;

D O I：

10.1002/anie.201701147

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A Rh-II-catalyzed, formal [4+1]-cycloaddition between diazooxindoles as electrophilic C-1 synthons and 1,3-heterodienes for the construction of spirooxindole pyrrolones is described. Employing vinyl isocyanates as 1,4-dipoles, the cycloannulation occurs under relatively mild conditions and provides the corresponding pyrrolones in good to excellent yields.

引用

页码：6604 / 6608

页数：5

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