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Updated: Mar 13, 2026

Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
Visible-Light Promoted Distereodivergent Intramolecular Oxyamidation of Alkenes
Xiang Ren1, Qihang Guo1, Jianhui Chen1,2
1Department of Chemistry, Zhejiang University, Hangzhou, Zhejiang, 310058, P. R. China.
Abstract:
The visible-light-promoted diastereodivergent intramolecular oxyamination of alkenes is described to construct oxazolindinones, pyrrolidinones and imidazolidones via mild generation of primary amidyl radicals from functionalized hydroxylamines. A unique phenomenon of highly diastereoselective ring-opening of aziridines controlled by electron sacrifices was observed. Highly diastereoselective amino alcohols derivatives were obtained efficiently through this protocol in gram scales. The mechanistic studies suggested the isolatable anti-aziridine intermediates were generated quickly from primary amidyl radicals and the diastereoselectivities were controlled by pKa values of the electron sacrifices.
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