{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Riart-Ferrer X"],"funding":["National Institutes of Health","National Science Foundation Division of Chemistry","NIGMS NIH HHS"],"pagination":["1120-1134"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC8049175"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["7(4)"],"pubmed_abstract":["Organic azides have been increasingly employed as nitrogen sources for catalytic olefine aziridination due to their ease of preparation and generation of benign N<sub>2</sub> 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<sub>3</sub> for highly asymmetric aziridination of alkenes at room temperature. The resulting enantioenriched <i>N</i>-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."],"journal":["Chem"],"pubmed_title":["Metalloradical activation of carbonyl azides for enantioselective radical aziridination."],"pmcid":["PMC8049175"],"funding_grant_id":["R01 GM102554"],"pubmed_authors":["Riart-Ferrer X","Tao J","Jin LM","Lu H","Cui X","Zhang XP","Sang P","Xu H","Wojtas L"],"additional_accession":[]},"is_claimable":false,"name":"Metalloradical activation of carbonyl azides for enantioselective radical aziridination.","description":"Organic azides have been increasingly employed as nitrogen sources for catalytic olefine aziridination due to their ease of preparation and generation of benign N<sub>2</sub> 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<sub>3</sub> for highly asymmetric aziridination of alkenes at room temperature. The resulting enantioenriched <i>N</i>-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.","dates":{"release":"2021-01-01T00:00:00Z","publication":"2021 Apr","modification":"2025-04-04T10:17:52.007Z","creation":"2025-04-04T10:17:52.007Z"},"accession":"S-EPMC8049175","cross_references":{"pubmed":["33869888"],"doi":["10.1016/j.chempr.2021.03.001"]}}