Organic azides have been increasingly employed as nitrogen sources for catalytic olefine aziridination due to their ease of preparation and generation of benign N as the only byproduct. Among common organic azides, carbonyl azides have not been previously demonstrated as effective nitrogen sources for intermolecular olefin aziridination despite the synthetic utilities of N-carbonyl aziridines. As a new application of metalloradical catalysis, we have developed a catalytic system that can effectively employ the carbonyl azide TrocN for highly asymmetric aziridination of alkenes at room temperature. The resulting enantioenriched -Trocaziridines have been shown as valuable chiral synthons for stereoselective synthesis of other chiral aziridines and various chiral amines. The Co(II)-based metalloradical system, which proceeds with distinctive stepwise radical mechanism, may provide a general method for asymmetric synthesis of chiral aziridines from alkenes with organic azides.

Download full-text PDF

Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC8049175PMC
http://dx.doi.org/10.1016/j.chempr.2021.03.001DOI Listing

Publication Analysis

Top Keywords

organic azides
12
carbonyl azides
8
nitrogen sources
8
synthesis chiral
8
chiral aziridines
8
azides
5
metalloradical activation
4
activation carbonyl
4
azides enantioselective
4
enantioselective radical
4

Similar Publications

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!