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Cite the Following Article
Synthesis of chiral N-phosphoryl aziridines through enantioselective aziridination of alkenes with phosphoryl azide via Co(II)-based metalloradical catalysis
Jingran Tao, Li-Mei Jin and X. Peter Zhang
Beilstein J. Org. Chem. 2014, 10, 1282–1289.
https://doi.org/10.3762/bjoc.10.129
How to Cite
Tao, J.; Jin, L.-M.; Zhang, X. P. Beilstein J. Org. Chem. 2014, 10, 1282–1289. doi:10.3762/bjoc.10.129
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- Gross, P.; Im, H.; Laws, D.; Park, B.; Baik, M.-H.; Blakey, S. B. Enantioselective Aziridination of Unactivated Terminal Alkenes Using a Planar Chiral Rh(III) Indenyl Catalyst. Journal of the American Chemical Society 2024, 146, 1447–1454. doi:10.1021/jacs.3c10637
- Wang, D.-S.; Zhang, X. P. Oxidation: C-N Bond Formation by Oxidation (Aziridines). Comprehensive Chirality; Elsevier, 2024; pp 158–179. doi:10.1016/b978-0-32-390644-9.00024-x
- Ajayi, N. D.; Ajayi, S. A.; Boyi, J. O.; Olaniyi, O. O. Understanding the Chemistry of Nitrene and Highlighting its Remarkable Catalytic Capabilities as a Non-Heme Iron Enzyme. SSRN Electronic Journal 2024. doi:10.2139/ssrn.4682019
- Fanourakis, A.; Phipps, R. J. Catalytic, asymmetric carbon-nitrogen bond formation using metal nitrenoids: from metal-ligand complexes via metalloporphyrins to enzymes. Chemical science 2023, 14, 12447–12476. doi:10.1039/d3sc04661c
- Ward, R. M.; Hu, Y.; Tu, N. P.; Schomaker, J. M. Solvent Effects on the Chemo- and Site-Selectivity of Transition Metal-Catalyzed Nitrene Transfer Reactions: Alternatives to Chlorinated Solvents. ChemSusChem 2023, 17, e202300964. doi:10.1002/cssc.202300964
- Lee, K.; Seo, K.; Dehghany, M.; Hu, Y.; Trinh, A.; Schomaker, J. M. An Overview of N-Heterocycle Syntheses Involving Nitrene Transfer Reactions. Topics in Heterocyclic Chemistry; Springer International Publishing, 2023; pp 313–377. doi:10.1007/7081_2023_66
- Xiao, X.; Xu, K.; Gao, Z.-H.; Zhu, Z.-H.; Ye, C.; Zhao, B.; Luo, S.; Ye, S.; Zhou, Y.-G.; Xu, S.; Zhu, S.-F.; Bao, H.; Sun, W.; Wang, X.; Ding, K. Biomimetic asymmetric catalysis. Science China Chemistry 2023, 66, 1553–1633. doi:10.1007/s11426-023-1578-y
- Zerull, E.; Trinh, T. A.; Kim, J.; Schomaker, J. M. doi:10.1002/9783527834242.chf0139
- Ward, R. M.; Schomaker, J. M. doi:10.1002/9783527834242.chf0147
- Shioiri, T.; Ishihara, K.; Matsugi, M. Cutting edge of diphenyl phosphorazidate (DPPA) as a synthetic reagent – A fifty-year odyssey. Organic Chemistry Frontiers 2022, 9, 3360–3391. doi:10.1039/d2qo00403h
- Reek, J. N. H.; de Bruin, B.; Pullen, S.; Mooibroek, T. J.; Kluwer, A. M.; Caumes, X. Transition Metal Catalysis Controlled by Hydrogen Bonding in the Second Coordination Sphere. Chemical reviews 2022, 122, 12308–12369. doi:10.1021/acs.chemrev.1c00862
- Deng, T.; Mazumdar, W.; Yoshinaga, Y.; Patel, P. B.; Malo, D.; Malo, T.; Wink, D. J.; Driver, T. G. Rh2(II)-Catalyzed Intermolecular N-Aryl Aziridination of Olefins Using Nonactivated N Atom Precursors. Journal of the American Chemical Society 2021, 143, 19149–19159. doi:10.1021/jacs.1c09229
- Peng, X.-H.; Bai, R.; Liu, S.; Li, Z.; Jiao, L.-Y. Substitution of diarylphosphoryl azides with aliphatic amines catalyzed by simple rare-earth metal salts: Efficient and novel preparation of phosphoryl amides. Applied Organometallic Chemistry 2021, 36. doi:10.1002/aoc.6507
- Ju, M.; Schomaker, J. M. Nitrene transfer catalysts for enantioselective C–N bond formation. Nature reviews. Chemistry 2021, 5, 580–594. doi:10.1038/s41570-021-00291-4
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