title: Efficient Trapping of 1,2-Cyclohexadienes with 1,3-Dipoles.
abstract: 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.
authors.affiliation: Department of Chemistry, University of Alberta, E3-43 Gunning-Lemieux Chemistry Centre, Edmonton, AB., T6G 2G2, Canada), Fax.
authors.forename: Verner A
authors.initials: VA
authors.lastname: Lofstrand
authors.affiliation: Department of Chemistry, University of Alberta, E3-43 Gunning-Lemieux Chemistry Centre, Edmonton, AB., T6G 2G2, Canada), Fax. frederick.west@ualberta.ca.
authors.forename: Frederick G
authors.identifier: http://orcid.org/0000-0001-7419-2314
authors.initials: FG
authors.lastname: West
keywords: cyclic allenes; cycloadditions; heterocycles; organic chemistry; reactive intermediates