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Synfacts 2010(8): 0923-0923  
DOI: 10.1055/s-0030-1257827
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© Georg Thieme Verlag Stuttgart ˙ New York

Chemo- and Enantioselective Synthesis of 3-Allyl-3-aryl Oxindoles

Contributor(s): Hisashi Yamamoto, Dmitry L. Usanov
X. Luan, L. Wu, E. Drinkel, R. Mariz, M. Gatti, R. Dorta*
University of Zurich, Switzerland
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Publication History

Publication Date:
22 July 2010 (online)

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Significance

Oxindoles containing a quaternary carbon center in position 3 constitute a common structural motif in a number of biologically important molecules. The authors developed a direct palladium-mediated α-arylation protocol, which represents a more convenient approach compared to the two-step sequence of α-arylation-­allylation. A wide range of products was obtained with excellent yields and good to excellent enantio­selectivities (up to 94% ee). Very small amounts, if any, of Heck byproducts were detected.