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      Stereoselective Synthesis of Vinylsilanes by a Gold(I)-Catalyzed Acetylenic Sila-Cope Rearrangement

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      Journal of the American Chemical Society
      American Chemical Society (ACS)

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          Abstract

          Cationic tri-tert-butylphosphinegold(I) serves as a catalyst in the sila-Cope rearrangement of acetylenic allylsilanes. When phenol is employed as a nucleophile, the reaction allows for the stereoselective synthesis of vinylsilanes. Alternatively, use of methanol as a nucleophile leads to cyclic vinylsilanes, which can be viewed as latent vinylsilanes that are revealed on treatment with a mild Lewis acid. Thus, both of these reagents serve as useful reagents for stereoselective synthesis of trisubstituted olefins through transition-metal-catalyzed cross-coupling reactions.

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          Author and article information

          Journal
          Journal of the American Chemical Society
          J. Am. Chem. Soc.
          American Chemical Society (ACS)
          0002-7863
          1520-5126
          September 2006
          September 2006
          : 128
          : 35
          : 11364-11365
          Article
          10.1021/ja0636800
          16939254
          2edce46e-260e-45a3-9484-e996573346fb
          © 2006
          History

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