Synthesis of chiral N-phosphoryl aziridines through enantioselective aziridination of alkenes with phosphoryl azide via Co(II)-based metalloradical catalysis
The Co(II) complex of a new D2-symmetric chiral porphyrin 3,5-DiMes-QingPhyrin, [Co(P6)], can catalyze asymmetric aziridination of alkenes with bis(2,2,2-trichloroethyl)phosphoryl azide (TcepN3) as a nitrene source. This new Co(II)-based metalloradical aziridination is suitable for different aromati...
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Beilstein-Institut
2014-06-01
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| Series: | Beilstein Journal of Organic Chemistry |
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| Online Access: | https://doi.org/10.3762/bjoc.10.129 |
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doaj-3495b5188b384c689c18eff709df3bb32021-02-02T03:25:54ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972014-06-011011282128910.3762/bjoc.10.1291860-5397-10-129Synthesis of chiral N-phosphoryl aziridines through enantioselective aziridination of alkenes with phosphoryl azide via Co(II)-based metalloradical catalysisJingran Tao0Li-Mei Jin1X. Peter Zhang2Department of Chemistry, University of South Florida, Tampa, Florida 33620, USADepartment of Chemistry, University of South Florida, Tampa, Florida 33620, USADepartment of Chemistry, University of South Florida, Tampa, Florida 33620, USAThe Co(II) complex of a new D2-symmetric chiral porphyrin 3,5-DiMes-QingPhyrin, [Co(P6)], can catalyze asymmetric aziridination of alkenes with bis(2,2,2-trichloroethyl)phosphoryl azide (TcepN3) as a nitrene source. This new Co(II)-based metalloradical aziridination is suitable for different aromatic olefins, producing the corresponding N-phosphorylaziridines in good to excellent yields (up to 99%) with moderate to high enantioselectivities (up to 85% ee). In addition to mild reaction conditions and generation of N2 as the only byproduct, this new metalloradical catalytic system is highlighted with a practical protocol that operates under neutral and non-oxidative conditions.https://doi.org/10.3762/bjoc.10.129asymmetric aziridinationaziridinechiral porphyrincobalt complexmetalloradical catalysisorganophosphorusphosphoryl azide |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Jingran Tao Li-Mei Jin X. Peter Zhang |
| spellingShingle |
Jingran Tao Li-Mei Jin X. Peter Zhang Synthesis of chiral N-phosphoryl aziridines through enantioselective aziridination of alkenes with phosphoryl azide via Co(II)-based metalloradical catalysis Beilstein Journal of Organic Chemistry asymmetric aziridination aziridine chiral porphyrin cobalt complex metalloradical catalysis organophosphorus phosphoryl azide |
| author_facet |
Jingran Tao Li-Mei Jin X. Peter Zhang |
| author_sort |
Jingran Tao |
| title |
Synthesis of chiral N-phosphoryl aziridines through enantioselective aziridination of alkenes with phosphoryl azide via Co(II)-based metalloradical catalysis |
| title_short |
Synthesis of chiral N-phosphoryl aziridines through enantioselective aziridination of alkenes with phosphoryl azide via Co(II)-based metalloradical catalysis |
| title_full |
Synthesis of chiral N-phosphoryl aziridines through enantioselective aziridination of alkenes with phosphoryl azide via Co(II)-based metalloradical catalysis |
| title_fullStr |
Synthesis of chiral N-phosphoryl aziridines through enantioselective aziridination of alkenes with phosphoryl azide via Co(II)-based metalloradical catalysis |
| title_full_unstemmed |
Synthesis of chiral N-phosphoryl aziridines through enantioselective aziridination of alkenes with phosphoryl azide via Co(II)-based metalloradical catalysis |
| title_sort |
synthesis of chiral n-phosphoryl aziridines through enantioselective aziridination of alkenes with phosphoryl azide via co(ii)-based metalloradical catalysis |
| publisher |
Beilstein-Institut |
| series |
Beilstein Journal of Organic Chemistry |
| issn |
1860-5397 |
| publishDate |
2014-06-01 |
| description |
The Co(II) complex of a new D2-symmetric chiral porphyrin 3,5-DiMes-QingPhyrin, [Co(P6)], can catalyze asymmetric aziridination of alkenes with bis(2,2,2-trichloroethyl)phosphoryl azide (TcepN3) as a nitrene source. This new Co(II)-based metalloradical aziridination is suitable for different aromatic olefins, producing the corresponding N-phosphorylaziridines in good to excellent yields (up to 99%) with moderate to high enantioselectivities (up to 85% ee). In addition to mild reaction conditions and generation of N2 as the only byproduct, this new metalloradical catalytic system is highlighted with a practical protocol that operates under neutral and non-oxidative conditions. |
| topic |
asymmetric aziridination aziridine chiral porphyrin cobalt complex metalloradical catalysis organophosphorus phosphoryl azide |
| url |
https://doi.org/10.3762/bjoc.10.129 |
| work_keys_str_mv |
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