Catalytic asymmetric 1,3-dipolar cycloaddition of azomethine ylides with alpha,beta-unsaturated ketones.
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.
Hernández-Toribio
Jorge
J
Departamento de Química Orgánica, Facultad de Ciencias, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain.
Gómez Arrayás
Ramón
R
Martín-Matute
Belén
B
Carretero
Juan C
JC
D001391:Azo Compounds / Q000737:chemistry*; D002384:Catalysis; D007659:Ketones / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity; D013882:Thiosemicarbazones / Q000737:chemistry*
D001391:Azo Compounds; D007659:Ketones; D013882:Thiosemicarbazones; C512188:azomethine