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Synthesis 1988; 1988(3): 178-183
DOI: 10.1055/s-1988-27506
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Synthesis of 1,3-Dicarbonyl Compounds by the Oxidation of 3-Hydroxycarbonyl Compounds with Corey-Kim Reagent

Sadamu Katayama* , Kinue Fukuda, Toshio Watanabe, Masashige Yamauchi
  • *Faculty of Pharmaceutical Sciences, Josai University, Keyakidai, Sakado, Saitama 350-02, Japan
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Publication Date:
20 August 2002 (online)

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A new method for the preparation of various 1,3-dicarbonyl compounds is described. Oxidation of 3-hydroxycarbonyl compounds without substituent at C-2 position by the Corey-Kim reagent (N-chlorosuccinimide-dimethyl sulfide) afforded the stable dimethylsulfonium methylides, which on reductive desulfurization by zinc-acetic acid furnished the 1,3-dicarbonyl derivatives.On the other hand, the same treatment of 2-mono-, or 2,2-disubstituted 3-hydroxy-carbonyl compounds gave directly the corresponding 1,3-dicarbonyl analogous,respectively.