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Updated: Mar 14, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
A Route to Polysubstituted Aziridines from Carbenes and Imines through a Nondiazo Approach
Hejiang Luo1, Kai Chen1, Huanfeng Jiang1
1Key Laboratory of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology , Guangzhou 510640, P. R. China.
Abstract:
An efficient method for the synthesis of polysubstituted aziridines utilizing enynones and imines is described. This transformation is achieved through the reaction of imines with donor/donor carbene intermediates, which were generated in situ from the cyclization of enynones. Furthermore, the resulted aziridines were good 1,3-dipoles, which could be efficiently trapped by dipolarophiles to give five-membered heterocycles. The obvious advantages of wide substrate scopes, mild reaction conditions, and high atom efficiency make this system highly appealing for construction of polysubstituted aziridines, 2,5-dihydropyroles, and 1,2,4-triazolidines.
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