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

Chem Sci

January 2024

Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science, Soochow University 199 Ren-Ai Road Suzhou Jiangsu 215123 China

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.

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