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Visible‐Light Promoted Distereodivergent Intramolecular Oxyamidation of Alkenes
Author(s) -
Ren Xiang,
Guo Qihang,
Chen Jianhui,
Xie Hujun,
Xu Qing,
Lu Zhan
Publication year - 2016
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201603977
Subject(s) - aziridine , intramolecular force , radical , chemistry , primary (astronomy) , ring (chemistry) , pyrrolidinones , combinatorial chemistry , stereochemistry , organic chemistry , physics , astronomy
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 p K a values of the electron sacrifices.