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
收藏
页码：6604 / 6608
页数：5
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