Enantioselective cycloaddition of münchnones onto [60]fullerene: organocatalysis versus metal catalysis.
Novel chiral catalytic systems based on both organic compounds and metal salts have been developed for the enantioselective [3 + 2] cycloaddition of münchnones onto fullerenes and olefins. These two different approaches proved to be efficient and complementary in the synthesis of optically active pyrrolino[3,4:1,2][60]fullerenes with high levels of enantiomeric excess and moderate to good conversions. Further functionalization of the pyrrolinofullerene carboxylic acid derivatives has been carried out by esterification and amidation reactions.
Departamento de Química Orgánica I, Facultad de Química, Universidad Complutense , E-28040 Madrid, Spain.
Juan
J
Marco-Martínez
Silvia
S
Reboredo
Marta
M
Izquierdo
Vanesa
V
Marcos
Juan Luis
JL
López
Salvatore
S
Filippone
Nazario
N
Martín
D002384:Catalysis; D061565:Cycloaddition Reaction; D037741:Fullerenes / Q000737:chemistry*; D008024:Ligands; D008301:Maleimides / Q000737:chemistry; D008670:Metals / Q000737:chemistry*; D009930:Organic Chemicals / Q000737:chemistry*; D010080:Oxazoles / Q000737:chemistry*; D010081:Oxazolone / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
D037741:Fullerenes; D008024:Ligands; D008301:Maleimides; D008670:Metals; D009930:Organic Chemicals; D010080:Oxazoles; D010081:Oxazolone; C028525:N-phenylmaleimide; C069837:fullerene C60