1609548-96-0Relevant academic research and scientific papers
Asymmetric Ring-Closing Aminooxygenation of Alkenes en Route to 2-Amino-1,3-Diols with Vicinal Stereocenters
Tan, Yuqi,Han, Feng,Hemming, Marcel,Wang, Jie,Harms, Klaus,Xie, Xiulan,Meggers, Eric
, p. 6653 - 6656 (2020)
A ring-closing aminooxygenation of alkenes with N-benzoyloxycarbamates occurs with very high diastereoselectivity (typically >20:1 d.r.) and very high enantioselectivity (up to 99percent ee). The reaction is catalyzed by a recently developed chiral-at-metal ruthenium complex at catalyst loadings of 0.5-1.0 mol percent. The reaction is proposed to proceed through a ruthenium nitrenoid intermediate that depending on the nature of the substrate undergoes either an aminooxygenation (1,2-disubstituted alkenes) or stops at the stage of the aziridination (trisubstituted alkenes), which can then be ring opened with benzoic acid. The resulting chiral cyclic carbamates can be hydrolyzed under basic conditions to provide versatile chiral 2-amino-1,3-diols with vicinal stereocenters.
Visible-Light Promoted Distereodivergent Intramolecular Oxyamidation of Alkenes
Ren, Xiang,Guo, Qihang,Chen, Jianhui,Xie, Hujun,Xu, Qing,Lu, Zhan
, p. 18695 - 18699 (2016/12/26)
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 pKavalues of the electron sacrifices.
