title: Synthesis of Functionalized Cyclopentene Derivatives from Vinyldiazo Compounds and Vinylazides through Sequential Copper-Promoted [3+2] Cycloaddition/Azide Rearrangement.
abstract: The reaction of vinylazides with alkenyldiazo compounds in the presence of [Cu(CH3CN)4][BF4] provided cyclopentene derivatives with retention of the azide functionality. This process likely involves a sequence comprising: 1) decomposition of the diazo component with generation of a copper alkenylcarbene species; 2) stepwise regioselective [3+2] cycloaddition; 3) allylic azide rearrangement. This method is compatible with a broad range of substrates. We also show that the azide-containing cycloadducts can be efficiently converted into the corresponding amine and triazole derivatives.
authors.affiliation: Departmento de Química Orgánica e Inorgánica and Instituto Universitario de Química Organometálica "Enrique Moles", Universidad de Oviedo, Julián Clavería 8, 33006-, Oviedo, Spain.
authors.forename: Enol
authors.initials: E
authors.lastname: López
authors.affiliation: Departmento de Química Orgánica e Inorgánica and Instituto Universitario de Química Organometálica "Enrique Moles", Universidad de Oviedo, Julián Clavería 8, 33006-, Oviedo, Spain.
authors.forename: Luis A
authors.initials: LA
authors.lastname: López
keywords: [3+2] cycloaddition; azides; copper; cyclopentenes; diazo compounds