Effective Synthesis of Chiral N-Fluoroaryl Aziridines through Enantioselective Aziridination of Alkenes with Fluoroaryl Azides


  • We are grateful for financial support by NSF (CHE-1152767) and NIH (R01-GM098777. We thank the Advanced Photon Source at Argonne National Lab, Chicago, IL for the measurement of the X-ray structure of porphyrin P3.


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The CoII complex of a D2-symmetric chiral porphyrin ([Co(D2-Por*)], see scheme) is a highly effective catalyst for the enantioselective aziridination of alkenes with fluoroaryl azides. The reaction can be performed at RT with low catalyst loading, and the olefin is the limiting reagent. Furthermore, the reaction is tolerant toward different combinations of aromatic olefins and fluoroaryl azides.