Stereodivergent‐at‐Metal Synthesis of [60]Fullerene Hybrids

Chiral fullerene–metal hybrids with complete control over the four stereogenic centers, including the absolute configuration of the metal atom, have been synthesized for the first time. The stereochemistry of the four chiral centers formed during [60]fullerene functionalization is the result of both...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2017-02, Vol.56 (8), p.2136-2139
Main Authors: Marco‐Martínez, Juan, Vidal, Sara, Fernández, Israel, Filippone, Salvatore, Martín, Nazario
Format: Article
Language:English
Subjects:
Absolute configuration
Catalysts
chiral metallofullerenes
chiral-at-metal complexes
Coordination compounds
enantioselective synthesis
fullerene chemistry
Fullerenes
Hybrids
Iridium
Metal complexes
Metals
Rhodium
Ruthenium
Stereochemistry
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Summary:Chiral fullerene–metal hybrids with complete control over the four stereogenic centers, including the absolute configuration of the metal atom, have been synthesized for the first time. The stereochemistry of the four chiral centers formed during [60]fullerene functionalization is the result of both the chiral catalysts employed and the diastereoselective addition of the metal complexes used (iridium, rhodium, or ruthenium). DFT calculations underpin the observed configurational stability at the metal center, which does not undergo an epimerization process. Chirality at the metal: Fullerene hybrids with iridium‐, rhodium‐, or ruthenium‐centered chirality were prepared by precise control of four newly formed stereogenic centers. The resulting complexes are configurationally stable and do not undergo an epimerization process.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201611475