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Enantioselective cycloaddition of munchnones onto [60]fullerene: organocatalysis versus metal catalysis.

ABSTRACT: 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.

SUBMITTER: Marco-Martinez J

PROVIDER: S-EPMC3954715 | biostudies-literature | 2014 Feb

REPOSITORIES: biostudies-literature

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Enantioselective cycloaddition of münchnones onto [60]fullerene: organocatalysis versus metal catalysis.

Marco-Martínez Juan J Reboredo Silvia S Izquierdo Marta M Izquierdo Marta M Marcos Vanesa V López Juan Luis JL Filippone Salvatore S Martín Nazario N

Journal of the American Chemical Society 20140210 7

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 carrie ...[more]

PMID: 24483247

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