Synthesis of donor-acceptor alkynylcyclopropanes by diastereoselective cyclopropanation of electron-deficient alkenes with alkoxyalkynyl Fischer carbene complexes.
The reaction of electron-deficient alkenes with alkoxyalkynyl Fischer carbene complexes (FCCs) represents a straightforward route to a new type of captodative (donor-acceptor) alkynylcyclopropanes, which have been prepared in moderate to high yields and in a diastereoselective manner. Some studies regarding the employment of additives to facilitate the recovery of the metal moiety after the reaction are also described. Finally, the first example of a cyclopropanation reaction through employing Fischer carbene complexes under microwave irradiation is presented; this method proved to be an advantageous alternative to the thermal reaction.
Barluenga
José
J
Instituto Universitario de Química Organometálica Enrique Moles, Unidad Asociada al C.S.I.C., Universidad de Oviedo, C/Julián Clavería, 8, 33006 Oviedo, Spain. barluenga@uniovi.es
Fernández-Rodríguez
Manuel A
MA
García-García
Patricia
P
Aguilar
Enrique
E
Merino
Isabel
I
D000475:Alkenes / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D003500:Cyclization; D003521:Cyclopropanes / Q000138:chemical synthesis* / Q000737:chemistry; D004583:Electrons; D006838:Hydrocarbons / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D008872:Microwaves; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
D000475:Alkenes; D000480:Alkynes; D003521:Cyclopropanes; D006838:Hydrocarbons; C030011:carbene; D008697:Methane