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Synfacts 2009(10): 1116-1116  
DOI: 10.1055/s-0029-1217838
Metal-Catalyzed Asymmetric Synthesis and Stereoselective Reactions
© georg thieme verlag stuttgart ˙ new york

Pd-Catalyzed Asymmetric α-Arylation and α-Vinylation of Oxindoles

Contributor(s): Hisashi Yamamoto, Cheol Hong Cheon
A. M. Taylor, R. A. Altman, S. L. Buchwald*
Massachusetts Institute of Technology, Cambridge, USA
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Publication History

Publication Date:
22 September 2009 (online)

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Significance

The authors have developed the Pd-catalyzed enantioselective α-arylation and α-vinylation of oxindoles using a ligand with both axial and phosphorus-based chirality. The products having all-carbon quaternary centers were obtained with excellent enantioselectivities and in good yields. Moreover, the α-aryl and α-vinyl oxindole products were further derivatized without any loss of optical activity.