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Synthesis of Polysubstituted Pyrroles through a Formal [4 + 1] Cycloaddition/E1cb Elimination/Aromatization Sequence of Sulfur Ylides and α,β-Unsaturated Imines

Bei-Yi Cheng, Ya-Ni Wang, Tian-Ren Li, Liang-Qiu Lu* and Wen-Jing Xiao*

*Key Laboratory of Pesticide & Chemical Biology, College of Chemistry, Central China Normal University, 152 Luoyu Road, Wuhan, Hubei 430079, China, Email: luliangqiumail.ccnu.edu.cn, wxiaomail.ccnu.edu.cn

B.-Y. Chen, Y.-N. Wang, T.-R. Li, L.-Q. Lu, W.-J. Xiao, J. You, J. Org. Chem., 2017, 82, 12134-12140.

DOI: 10.1021/acs.joc.7b01931 (free Supporting Information)


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Abstract

A formal [4 + 1] cycloaddition of sulfur ylides with α,β-unsaturated imines followed by an E1cb elimination and an aromatization process provides polysubstituted pyrroles. This protocol offers mild conditions, high efficiency, and a wide substrate scope.

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proposed reaction pathway



Key Words

Pyrroles


ID: J42-Y2017