Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 22, Issue 34, Pages 11977-11981Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201602372
Keywords
alkynylation; asymmetric catalysis; chirality; cyclometalation; rhodium; trifluoromethyl
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Funding
- German Research Foundation [ME 1805/13-1]
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Chiral rhodium(III) complexes containing two cyclometalating 2-phenyl-5,6-(S,S)-pinenopyridine ligands and two additional acetonitriles are introduced as excellent catalysts for the highly enantioselective alkynylation of 2-trifluoroacetyl imidazoles. Whereas the ligand-based chirality permits the straightforward synthesis of the complexes in a diastereomerically and enantiomerically pure fashion, the metal-centered chirality is responsible for the asymmetric induction over the course of the catalysis. For comparison, the analogous iridium congeners provide only low enantioselectivity, and previously reported benzoxazole- and benzothiazole-based catalysts do not show any catalytic activity for this reaction under standard reaction conditions.
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