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Copper(I)-catalyzed asymmetric alkene aziridination mediated by PhI(OAc)2: a facile one-pot procedure |
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| Authors: | Hoi-Lun Kwong Di Liu Chi-Sing Lee Chi-Ming Che |
| Affiliation: | a Department of Biology and Chemistry and Open Laboratory of Chirotechnology of the Institute of Molecular Technology for Drugs Discovery and Synthesis, City University of Hong Kong, Tat Chee Avenue, Kowloon Tong, Hong Kong SAR, China b Department of Chemistry and Open Laboratory of Chemical Biology of the Institute of Molecular Technology for Drugs Discovery and Synthesis, The University of Hong Kong, Pokfulam Road, Hong Kong SAR, China |
| Abstract: | A facile one-pot procedure for copper-catalyzed PhI(OAc)2-mediated asymmetric alkene aziridination had been developed. Commercially available PhI(OAc)2 and sulfonamides were used to generate the nitrene precursors (PhINR) in situ for olefin aziridination. This one-pot procedure had been optimized using 4-nitrobenzenesulfonamide as the nitrene source. With 5 mol % of the chiral copper catalyst, these conditions afforded 94% yield of the isolated product with 75% ee. We had also developed a simple and rapid method to monitor the rate of this one-pot aziridination. |
| Keywords: | One-pot asymmetric aziridination Copper catalyst Styrene Iodobenzene diacetate Sulfonamides |
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