Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 26, Issue 7, Pages 1501-1505Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201904727
Keywords
aryl anions; arynes; DFT calculations; strained rings; vinyl aziridines
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Funding
- Natural Science and Engineering Research Council (NSERC)
- Deutsche Forschungsgemeinschaft (DFG)
- NSERC
- University of Toronto
- Canadian Foundation for Innovation [19119]
- Ontario Research Fund
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We report the cycloaddition between vinyl aziridines and arynes. Depending on the reaction conditions and the choice of the aryne precursor, the aziridinium intermediate can be trapped through two distinct mechanistic pathways. The first one proceeds through a formal [5+2] cycloaddition to furnish valuable multi-substituted benzazepines. In the second pathway, the aziridinium is intercepted by a fluoride ion to afford allylic fluorides in good yields. Both reactions proceed stereospecifically and furnish enantiopure benzazepines and allylic fluorides.
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