Synthesis of Chiral N-Heterocyclic Carbene Ligands with Rigid Backbones and Application to the Palladium-Catalyzed Enantioselective Intramolecular α-Arylation of Amides

Lantao Liu, Naoki Ishida, Shinji Ashida and Masahiro Murakami*

*Department of Synthetic Chemistry and Biological Chemistry, Kyoto University, Katsura, Kyoto 615-8510, Japan, Email: murakamisbchem.kyoto-u.ac.jp

L. Liu, N. Ishida, S. Ashida, M. Murakami, Org. Lett., 2011, 13, 1666-1669.

DOI: 10.1021/ol200149s

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Abstract

Chiral N-heterocyclic carbene (NHC) ligands having a 2,2′-bisquinoline-based C₂ symmetric skeleton exhibited good enantioselectivity in palladium-catalyzed intramolecular α-arylation of amides to give 3,3-disubsituted oxindoles.

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Key Words

α-arylation, oxindoles

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ID: J54-Y2011-0850