Phosphine-catalyzed regiospecific (3+2) cyclization of 3-nitroindoles with allene esters

被引：27
|
作者：
Jin, Li-Wen [1 ]
Jiang, Fei [1 ]
Chen, Ke-Wei [1 ]
Du, Bai-Xiang [1 ]
Mei, Guang-Jian [1 ]
Shi, Feng [1 ]
机构：
[1] Jiangsu Normal Univ, Sch Chem & Mat Sci, Xuzhou 221116, Jiangsu, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2019年 / 17卷 / 16期
关键词：
HIGHLY ENANTIOSELECTIVE SYNTHESIS; ASYMMETRIC DEAROMATIZATION; 4+2 ANNULATION; 3-ISOTHIOCYANATO OXINDOLES; 1,3-DIPOLAR CYCLOADDITION; AZOMETHINE YLIDES; QUINONE METHIDES; CASCADE REACTION; INDOLES; CONSTRUCTION;
D O I：
10.1039/c9ob00432g
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A phosphine-catalyzed regiospecific (3 + 2) cyclization of 3-nitroindoles with allene esters has been established, which constructed indole-fused five-membered rings in good yields (up to 86%). This reaction serves as a powerful method for the construction of indole-fused five-membered rings. In addition, this reaction provides a useful strategy toward settling the challenge of utilizing other 1,3-dipoles or 1,3dipole surrogates to perform (3 + 2) cyclizations with 3-nitroindoles in different catalytic modes, which will enrich the chemistry of nitroindoles and catalytic asymmetric dearomatization cyclizations.
引用
收藏
页码：3894 / 3901
页数：8
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