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

J Am Chem Soc

Departamento de Química Orgánica I, Facultad de Química, Universidad Complutense , E-28040 Madrid, Spain.

Published: February 2014

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.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3954715PMC
http://dx.doi.org/10.1021/ja500071kDOI Listing

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