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Updated: Jul 12, 2025

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Radical-Based cis-Selective Annulations of N,N'-Cyclic Azomethine Imines with N-Sulfonyl Cyclopropylamines
Jie Qiu1, Wei Li1, Xiaofeng Li1
1State Key Laboratory for Chemistry and Molecular Engineering of Medicinal Resources, School of Chemistry and Pharmaceutical Sciences, Guangxi Normal University, Guilin 541004, China.
Abstract:
Azomethine imines, broadly known as 1,3-dipoles, efficiently produce synthetically and biologically significant dinitrogen-fused heterocycles via predominantly concerted or ionic pathways. Herein, we describe a radical-based annulation of azomethine imines utilizing visible-light photoredox catalysis for the first time. This strategy enables the synthesis of dinitrogen-fused saturated six-membered cyclic products that have traditionally been difficult to access. Notably, our process exhibits exceptional cis diastereoselectivity, controlled by the anomeric effect. Initial mechanistic investigations reveal a tandem process comprising intermolecular radical addition and intramolecular 6-exo-trig cyclization. This work illustrates potential within the realm of visible-light-driven radical cyclization reactions involving azomethine imines.
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