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Updated: Feb 26, 2026

Preparation of Stable Bicyclic Aziridinium Ions and Their Ring-Opening for the Synthesis of Azaheterocycles
Published on: August 22, 2018
Facile Synthesis of Azetidine Nitrones and Diastereoselective Conversion into Densely Substituted Azetidines
Tyler W Reidl1, Jongwoo Son1, Donald J Wink1
1Department of Chemistry, University of Illinois at Chicago, 845 W. Taylor St., Chicago, IL, USA.
Abstract:
An electrocyclization route to azetidine nitrones from N-alkenylnitrones was discovered that provides facile access to these unsaturated strained heterocycles. Reactivity studies showed that these compounds undergo a variety of reduction, cycloaddition, and nucleophilic addition reactions to form highly substituted azetidines with excellent diastereoselectivity. Taken together, these transformations provide a fundamentally different approach to azetidine synthesis than traditional cyclization by nucleophilic displacement and provide novel access to a variety of underexplored strained heterocyclic compounds.
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