Organocatalytic β‑Azidation of Enones Initiated by an Electron-Donor–Acceptor Complex

An operationally straightforward organocatalytic β-azidation of α,β-unsaturated ketones is described. Reaction of the Zhdankin azidoiodane with enones in the presence of a catalytic amount of an amine provides β-azido ketones via the formation of an electron-donor–acceptor complex. The application o...

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Bibliographic Details
Published in:Organic letters 2017-10, Vol.19 (19), p.5482-5485
Main Authors: Shirke, Rajendra P, Ramasastry, S. S. V
Format: Article
Language:English
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Summary:An operationally straightforward organocatalytic β-azidation of α,β-unsaturated ketones is described. Reaction of the Zhdankin azidoiodane with enones in the presence of a catalytic amount of an amine provides β-azido ketones via the formation of an electron-donor–acceptor complex. The application of this protocol is demonstrated through one-step elaborations leading to the synthesis of unprecedented classes of 1,2,3-triazoles.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b02861