Catalytic Asymmetric Dearomative [3+2] Cycloaddition of Electron-Deficient Indoles with All-Carbon 1,3-Dipoles

被引：82

作者：

Sun, Meng ^{[1
]}

Zhu, Zi-Qi ^{[1
]}

Gu, Ling ^{[1
]}

Wan, Xiao ^{[1
]}

Mei, Guang-Jian ^{[1
]}

Shi, Feng ^{[1
]}

机构：

[1] Jiangsu Normal Univ, Sch Chem & Mat Sci, Xuzhou 221116, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2018年 / 83卷 / 04期

基金：

中国国家自然科学基金;

关键词：

VINYL CYCLOPROPANES; AZOMETHINE YLIDES; ENANTIOSELECTIVE SYNTHESIS; 3-ISOTHIOCYANATO OXINDOLES; ARYLATIVE DEAROMATIZATION; QUINONE METHIDES; CASCADE REACTION; 3-NITROINDOLES; CONSTRUCTION; ACCESS;

D O I：

10.1021/acs.joc.7b03259

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first catalytic asymmetric dearomative [3 + 2] cycloaddition of 3-nitroindoles with vinylcyclopropanes has been established, which constructed chiral cyclopenta[b]-indoline scaffolds in generally high enantioselectivities (up to 97% ee). This reaction also represents the first application of all-carbon 1,3-dipoles in catalytic asymmetric dearomative [3 + 2] cycloadditions of 3-nitroindoles. This approach will not only advance the catalytic asymmetric dearomatization reactions of electron-deficient indoles but also provide an efficient method for constructing chiral cyclopenta[b]indoline scaffolds.

引用

页码：2341 / 2348

页数：8

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