Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 131, Issue 24, Pages 8344-+Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ja901018g
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Funding
- Fonds der Chemischen Industrie
- Deutsche Forschungsgemeinschaft
- Alfried Krupp von Bohlen und Halbach Foundation (Alfried Krupp Prize for Young University Teachers)
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An exceedingly sterically demanding, rigid, and chiral NHC ligand, IBiox[(-)-menthyl] (1), was prepared and structurally characterized. With a buried volume of similar to 50%, this ligand arguably represents one of the most sterically demanding monodentate ligands. The ability to use aryl chloride substrates in intramolecular palladium-catalyzed alpha-arylations reveals its unique reactivity. Moreover, C-2-symmetric 1 allows the highly enantioselective formation of oxindoles with up to 99% ee.
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