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

被引：30

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

页码：3894 / 3901

页数：8

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