title: Zinc-catalyzed alkene cyclopropanation through zinc vinyl carbenoids generated from cyclopropenes.
abstract: The zinc-catalyzed reaction of cyclopropenes with alkenes leading to vinylcyclopropane derivatives is reported. A broad range of alkenes (including highly substituted or functionalized alkenes) is compatible with this protocol. On the basis of trapping experiments and computational studies, this cyclopropanation reaction is proposed to proceed through initial formation of an electrophilic zinc vinyl carbenoid intermediate, which may be involved in a concerted cyclopropanation reaction. The reported protocol represents an unprecedented and simple strategy for the catalytic generation of zinc vinyl carbenoids, which are promising intermediates in organic synthesis.
authors: Departamento de Química Orgánica e Inorgánica, Instituto Universitario de Química Organometálica "Enrique Moles", Universidad de Oviedo, c/Julián Clavería 8, 33006-Oviedo (Spain).
authors: María J
authors: MJ
authors: González
authors: Departamento de Química Orgánica e Inorgánica, Instituto Universitario de Química Organometálica "Enrique Moles", Universidad de Oviedo, c/Julián Clavería 8, 33006-Oviedo (Spain).
authors: Javier
authors: J
authors: González
authors: Departamento de Química Orgánica e Inorgánica, Instituto Universitario de Química Organometálica "Enrique Moles", Universidad de Oviedo, c/Julián Clavería 8, 33006-Oviedo (Spain). lalg@uniovi.es.
authors: Luís A
authors: LA
authors: López
authors: Departamento de Química Orgánica e Inorgánica, Instituto Universitario de Química Organometálica "Enrique Moles", Universidad de Oviedo, c/Julián Clavería 8, 33006-Oviedo (Spain). vicenteruben@uniovi.es.
authors: Rubén
authors: R
authors: Vicente
keywords: alkenes; carbenes; density functional calculations; small-ring compounds; zinc