Related Experiment Video
Updated: Feb 27, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Asymmetric Radical Bicyclization of Allyl Azidoformates via Cobalt(II)-Based Metalloradical Catalysis
Huiling Jiang1, Kai Lang2, Hongjian Lu1
1Department of Chemistry, University of South Florida , Tampa, Florida 33620, United States.
Abstract:
Cobalt(II)-based metalloradical catalysis has been successfully applied to radical bicyclization of allyl azidoformates to construct aziridine/oxazolidinone-fused bicyclic structures. The Co(II) complex of D2-symmetric chiral amidoporphyrin 3,5-DitBu-QingPhyrin has been identified as an effective metalloradical catalyst for the intramolecular radical aziridination of this type of carbonyl azides, allowing for high-yielding formation of synthetically useful chiral [3.1.0]-bicyclic aziridines with high diastereo- and enantioselectivity.
Related Concept Videos
Radical Substitution: Allylic Bromination
Radical Oxidation of Allylic and Benzylic Alcohols
Radical Anti-Markovnikov Addition to Alkenes: Overview
Radical Substitution: Allylic Chlorination
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
Radical Formation: Addition
Similar to charge conservation in chemical reactions, spin conservation is implicit for radical reactions. Accordingly, the product formed must possess an...

