Dearomatization of 3-Nitroindoles by a Phosphine-Catalyzed Enantioselective [3+2] Annulation Reaction

被引：95
|
作者：
Li, Kaizhi [1 ]
Goncalves, Theo P. [3 ,4 ]
Huang, Kuo-Wei [3 ,4 ]
Lu, Yixin [1 ,2 ]
机构：
[1] Natl Univ Singapore, Dept Chem, Singapore 117543, Singapore
[2] Natl Univ Singapore, Suzhou Res Inst, 377 Lin Quan St,Suzhou Ind Pk, Suzhou 215123, Jiangsu, Peoples R China
[3] King Abdullah Univ Sci & Technol, KAUST Catalysis Ctr, Thuwal 239556900, Saudi Arabia
[4] King Abdullah Univ Sci & Technol, Div Phys Sci & Engn, Thuwal 239556900, Saudi Arabia
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2019年 / 58卷 / 16期
基金：
新加坡国家研究基金会; 中国国家自然科学基金;
关键词：
3+2] annulation; cyclopentaindolines; dearomatization; nitroindoles; organocatalysis; ASYMMETRIC DEAROMATIZATION; 3-ISOTHIOCYANATO OXINDOLES; CYCLOADDITION REACTION; CRYSTAL-STRUCTURE; CASCADE REACTION; DIELS-ALDER; CONSTRUCTION; DERIVATIVES; INDOLES; ACCESS;
D O I：
10.1002/anie.201900248
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The dearomatization of 3-nitroindoles through a chiral-phosphine-mediated [3+2] annulation reaction is described. This method makes use of readily available 3-nitroindoles as an aromatic feedstock and rapidly delivers a wide range of cyclopentaindoline alkaloid scaffolds in a highly enantioselective manner. Notably, phosphine-triggered cyclization has not been utilized previously in a dearomatization process.
引用
收藏
页码：5427 / 5431
页数：5
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