Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 31, Pages 10763-10767Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201602201
Keywords
cyclic allenes; cycloadditions; heterocycles; organic chemistry; reactive intermediates
Categories
Funding
- Natural Science and Engineering Research Council of Canada (NSERC)
- University of Alberta
- NSERC
- American Chemical Society
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1,2-Cyclohexadienes are transient intermediates that undergo rapid dimerization and intermolecular trapping with activated olefins and heteroatomic nucleophiles. Fluoride-mediated desilylative elimination of readily accessible 6-silylcyclohexene-1-triflates allows the mild, chemoselective, and functional-group tolerant generation of cyclic allene intermediates, which undergo efficient trapping reactions with stable 1,3-dipoles. The reactions proceed with high levels of both regio- and diastereoselectivity. The reaction of cyclic allenes with azides is accompanied by the facile loss of dinitrogen, resulting in the formation of tetrahydroindoles or polycylic aziridines depending on the azide employed.
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