Issue 5, 2024

Access to pyrrolines and fused diaziridines by selective radical addition to homoallylic diazirines

Abstract

Pyrroline derivatives are common in bioactive natural products and therapeutic agents. We report here a synthesis of pyrrolines and fused diaziridines by divergent radical cyclization of homoallylic diazirines, which can serve as an internal radical trap and a nitrogen source. This reaction proceeds by selective radical addition to C[double bond, length as m-dash]C or N[double bond, length as m-dash]N bonds followed by intramolecular cyclization. Frontier molecular orbital analysis provides a deep insight into the origin of the selectivity. The reaction demonstrates a new cyclization mode, broad functional group compatibility and high product diversity, and reveals a much broader chemical space for diazirine studies.

Graphical abstract: Access to pyrrolines and fused diaziridines by selective radical addition to homoallylic diazirines

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Article information

Article type
Edge Article
Submitted
16 sen 2023
Accepted
28 dek 2023
First published
29 dek 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2024,15, 1879-1884

Access to pyrrolines and fused diaziridines by selective radical addition to homoallylic diazirines

Z. Ma, X. Wu, H. Li, Z. Cao and C. Zhu, Chem. Sci., 2024, 15, 1879 DOI: 10.1039/D3SC04886A

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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