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

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 al...

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Bibliographic Details
Published in:Journal of organic chemistry 2018-02, Vol.83 (4), p.2341-2348
Main Authors: Sun, Meng, Zhu, Zi-Qi, Gu, Ling, Wan, Xiao, Mei, Guang-Jian, Shi, Feng
Format: Article
Language:English
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b03259