Four-membered azetidine heterocycles have favorable pharmaceutical properties, including metabolic resistance and lowered lipophilicity, and introduces a three-dimensional sp3 scaffold. While azetidines are increasingly sought after in potential drug candidates, their synthesis is not straightforward. Recently, the development of [2+2] cycloadditions of alkenes with oximes has expanded the scope of accessible azetidines, but limitations still exist for molecular complexity and functional group tolerance. Herein is demonstrated an intramolecular [2+2] cycloaddition that expands access to tricyclic azetidine scaffolds in moderate to good yield. Further derivatization via hydrogenolysis of the N-O bond gives access to the free azetidine. This overall transformation provides a complimentary scaffold to existing aza Paternò-Büchi reactions.

Intramolecular, visible light-mediated aza Paternò-Büchi reactions of unactivated alkenes

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ACS Fall 2022

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.