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Stereodivergent synthesis of chiral fullerenes by [3 + 2] cycloadditions to C??.


ABSTRACT: A wide range of new dipoles and catalysts have been used in 1,3-dipolar cycloadditions of N-metalated azomethine ylides onto C60 yielding a full stereodivergent synthesis of pyrrolidino[60]fullerenes with complete diastereoselectivities and very high enantioselectivities. The use of less-explored chiral ?-iminoamides as starting 1,3-dipoles leads to an interesting double asymmetric induction resulting in a matching/mismatching effect depending upon the absolute configuration of the stereocenter in the starting ?-iminoamide. An enantioselective process was also found in the retrocycloaddition reaction as revealed by mass spectrometry analysis on quasi-enantiomeric pyrrolidino[60]fullerenes. Theoretical DFT calculations are in very good agreement with the experimental data. On the basis of this agreement, a plausible reaction mechanism is proposed.

SUBMITTER: Maroto EE 

PROVIDER: S-EPMC3914395 | biostudies-literature | 2014 Jan

REPOSITORIES: biostudies-literature

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Stereodivergent synthesis of chiral fullerenes by [3 + 2] cycloadditions to C₆₀.

Maroto Enrique E EE   Filippone Salvatore S   Suárez Margarita M   Martínez-Álvarez Roberto R   de Cózar Abel A   Cossío Fernando P FP   Martín Nazario N  

Journal of the American Chemical Society 20140103 2


A wide range of new dipoles and catalysts have been used in 1,3-dipolar cycloadditions of N-metalated azomethine ylides onto C60 yielding a full stereodivergent synthesis of pyrrolidino[60]fullerenes with complete diastereoselectivities and very high enantioselectivities. The use of less-explored chiral α-iminoamides as starting 1,3-dipoles leads to an interesting double asymmetric induction resulting in a matching/mismatching effect depending upon the absolute configuration of the stereocenter  ...[more]

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