title: Catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides with alpha,beta-unsaturated ketones.
abstract: Alpha,beta-unsaturated ketones are no longer the missing dipolarophiles in catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides. In the presence of Cu(I)-Fesulphos complexes as catalysts (5 mol %), these substrates combine high reactivity, wide substitution tolerance, moderate to good endo/exo selectivities, and high enantiocontrol. The endo/exo-diastereoselectivity of the reaction is strongly dependent on the cis or trans nature of the enone moiety.
authors.affiliation: Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain.
authors.forename: Jorge
authors.initials: J
authors.lastname: Hernández-Toribio
authors.forename: Ramón
authors.initials: R
authors.lastname: Gómez Arrayás
authors.forename: Belén
authors.initials: B
authors.lastname: Martín-Matute
authors.forename: Juan C
authors.initials: JC
authors.lastname: Carretero
mesh_terms: D001391:Azo Compounds / Q000737:chemistry*; D002384:Catalysis; D007659:Ketones / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity; D013882:Thiosemicarbazones / Q000737:chemistry*
chemical_list: D001391:Azo Compounds; D007659:Ketones; D013882:Thiosemicarbazones; C512188:azomethine