Visible-Light Promoted Distereodivergent Intramolecular Oxyamidation of Alkenes

作者:Ren, Xiang; Guo, Qihang; Chen, Jianhui; Xie, Hujun*; Xu, Qing*; Lu, Zhan*
来源:Chemistry - A European Journal, 2016, 22(52): 18695-18699.
DOI:10.1002/chem.201603977

摘要

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 pK(a) values of the electron sacrifices.