Asymmetric Organocatalysis in Fullerenes Chemistry: Enantioselective Phosphine-catalyzed Cycloaddition of Allenoates onto C60

• Published in: Angewandte Chemie International Edition Vol. 52; no. 19; pp. 5115 - 5119
• Main Authors: Marco-Martínez, Juan, Marcos, Vanesa, Reboredo, Silvia, Filippone, Salvatore, Martín, Nazario
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 03.05.2013; WILEY‐VCH Verlag; Wiley; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: 1,3‐dipolar cycloaddition; 3-dipolar cycloaddition; Absolute configuration; asymmetric catalysis; Asymmetry; Chemical synthesis; Chemistry; Chemistry, Multidisciplinary; Chirality; Cycloaddition; Enantiomers; enantioselectivity; fullerene; Fullerenes; organocatalysis; Phosphine; Phosphines; Physical Sciences; Science & Technology; enantioselectivity; CARBON; IMINES; 3-dipolar cycloaddition; 2,3-BUTADIENOATES; asymmetric catalysis; organocatalysis; 1; ALKENES; CYCLOPENTENES; C-60; CHIRALITY; DERIVATIVES; fullerene; ELECTRON-DEFICIENT OLEFINS
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.201301292

Organocatalysis and fullerenes merge: The first asymmetric organocatalytic synthesis by phosphine‐catalyzed [3+2] cycloaddition of allenoates onto [60]fullerene that occurs under mild conditions giving rise to enantiomerically pure carbocyclic fullerene derivatives is reported. X‐ray analysis of a cyclopenteno[60]fullerene has allowed the assignment of the absolute configuration of the new stereocenter. Furthermore, the sector rule previously used to assign the chirality in [60]fullerenes has been corrected in the light of these new experimental findings.