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Bifunctional organocatalysts for enantioselective aza-Morita-Baylis-Hillman reaction.

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      Abstract

      The efficient and novel bifunctional organocatalyst for the enantioselective aza-Morita-Baylis-Hillman (aza-MBH) reaction has been established with (S)-3-(N-isopropyl-N-3-pyridinylaminomethyl)BINOL for the first time. The reaction proved to be deeply influenced by the position of the Lewis base attached to BINOL. The acid-base-mediated functionalities for the activation of the substrate and the fixing of conformation of the organocatalyst are harmoniously performed to promote the reaction with high enantiocontrol.

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      Affiliations
      [1 ] The Institute of Scientific and Industrial Research (ISIR), Osaka University, Mihogaoka, Ibaraki, Osaka 567-0047, Japan.
      Journal
      J. Am. Chem. Soc.
      Journal of the American Chemical Society
      0002-7863
      0002-7863
      Mar 23 2005
      : 127
      : 11
      10.1021/ja0500254 15771486

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