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Asymmetric Radical Bicyclization of Allyl Azidoformates via Cobalt(II)-Based Metalloradical Catalysis

Author:
Jiang, Huiling, Lang, Kai, Lu, Hongjian, Wojtas, Lukasz, Zhang, X. Peter
Source:
Journal of the American Chemical Society 2017 v.139 no.27 pp. 9164-9167
ISSN:
1520-5126
Subject:
azides, aziridines, catalysts, catalytic activity, cobalt, enantioselectivity
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.
Agid:
6031222