Copper(I)-catalyzed [3+1] cycloaddition of alkenyldiazoacetates and iminoiodinanes: easy access to substituted 2-azetines.
The copper(I)-catalyzed reaction of alkenyldiazoacetates and iminoiodinanes affords functionalized azetine derivatives. This process is consistent with the formation of an aziridinyldiazoacetate intermediate, which gives rise to the four-membered heterocycles by metal-catalyzed ring expansion. The resulting azetine structure is a direct precursor of azeditine-2-carboxylic acid derivatives (EWG = electron-withdrawing group).
Instituto Universitario de Química Organometálica Enrique Moles, Universidad de Oviedo, Julián Clavería 8, 33006 Oviedo, Spain. barluenga@uniovi.es
José
J
Barluenga
Lorena
L
Riesgo
Giacomo
G
Lonzi
Miguel
M
Tomás
Luis A
LA
López
D001385:Azetines / Q000737:chemistry*; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D003500:Cyclization; D003979:Diazonium Compounds / Q000737:chemistry*; D054879:Halogenation; D007097:Imines / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction
D001385:Azetines; D003979:Diazonium Compounds; D007097:Imines; D003300:Copper