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Synfacts 2009(9): 1011-1011  
DOI: 10.1055/s-0029-1217638
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

A Sterically Demanding NHC Ligand

Contributor(s): Mark Lautens, Jacki Kitching
S. Würtz, C. Lohre, R. Fröhlich, K. Bergander, F. Glorius*
Westfälische Wilhelms-Universität Münster, Germany
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Publikationsdatum:
21. August 2009 (online)

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Significance

N-Heterocyclic carbene (NHC) ligands have recently shown widespread use in transition-metal catalysis. The present paper reports on the synthesis of a C 2-symmetric, sterically demanding NHC ligand and its application to the palladium-catalyzed asymmetric α-arylation of amides. The protocol successfully employs aryl bromides and chlorides as substrates and affords the corresponding oxindoles in high yield and with excellent enantioselectivities.