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Updated: Jan 13, 2026

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Iron-Catalyzed C-H Alkylative Ring Openings of Oxabicyclic Alkenes
Andrea Serafino1, Erika Barocelli1, Andrea Secchi1
1Dipartimento di Scienze Chimiche, della Vita e della Sostenibilità Ambientale, Università di Parma, Parco Area delle Scienze 17/A, I-43124 Parma, Italy.
Abstract:
We report the iron-catalyzed C-H alkylative ring openings of oxabicyclic alkenes by chelation assistance. The method converted a broad family of benzamides into highly functionalized dihydronaphthen-2-ol derivatives, amenable to further synthetic transformations by removing the triazole directing group. Remarkably, the iron catalysis displayed complete chemo- and regioselectivities in converting oxabicyclic alkenes functionalized at the bridgehead carbons. Mechanistic investigations, by means of DFT calculations, fully elucidated the mechanism of the iron catalysis.
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