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Synlett 1993; 1993(2): 133-134
DOI: 10.1055/s-1993-22376
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Reactions of 1-Aza-1,3-butadienes: A Simple Access to Bicyclo[3.3.1]nonan-3-one Derivatives

Jon K. F. Geirsson* , Jonina F. Johannesdottir, Sigridur Jonsdottir
  • *Science Institute, University of Iceland, Dunhaga 3, IS-107 Reykjavik, Iceland
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Publication Date:
19 March 2002 (online)

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A facile and efficient one-step procedure for the synthesis of bicyclo[3.3.1]nonan-3-one derivatives is described. Two equivalents of dimethyl 1,3-acetonedicarboxylate reacted with 1-aza-1,3-butadienes to afford the products in good to excellent yields (70-80%). The reaction proceeded with similar yields when the imine was replaced by the corresponding α,β-unsaturated aldehyde.