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Synfacts 2006(1): 0021-0021  
DOI: 10.1055/s-2005-921686
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Synthesis of 3-Benzylideneoxindoles

Contributor(s): Victor Snieckus, Robert Engqvist
R. Yanada, S. Obika, Y. Kobayashi, T. Inokuma, M. Oyama, K. Yanada, Y. Takemoto*
Kyoto University, Japan
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Publikationsdatum:
16. Dezember 2005 (online)

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Significance

The stereoselective synthesis of 3-benzylideneoxindoles from propynoic acid (2-iodophenyl) amides is reported. Treatment of the iodoaniline with In and Br2 leads to the incipient indium oxindole intermediate which, when subjected to direct Pd-catalyzed cross coupling with aryl iodides gives the benzylideneoxindoles. This tandem reaction proceeds in good yields and gives only one stereoisomer.