Radical-Based cis-Selective Annulations of N,N′‑Cyclic Azomethine Imines with N‑Sulfonyl Cyclopropylamines

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 catalysi...

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Bibliographic Details
Published in:Organic letters 2023-11, Vol.25 (44), p.8000-8004
Main Authors: Qiu, Jie, Li, Wei, Li, Xiaofeng, Cao, Yongyong, Pan, Cheng-Xue, Li, Huaifeng
Format: Article
Language:English
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Summary: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.3c03180