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Synlett 1993; 1993(9): 651-652
DOI: 10.1055/s-1993-22558
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Modification of the Fries Type Rearrangement of the O-Enol Acyl Group Using N,N-Dicyclohexyl-carbodiimide and 4-Dimethylaminopyridine

Hiroyasu Tabuchi* , Taisuke Hamamoto, Akitami Ichihara
  • *Department of Bioscience and Chemistry, Faculty of Agriculture, Hokkaido University, Sapporo 060, Japan
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Publication Date:
19 March 2002 (online)

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3-Acyl-5,6-dihydro-4-hydroxy-2-pyrones are prepared in one step from carboxylic acids and β-keto-δ-valerolactones using N,N-dicyclohexylcarbodiimide and 4-dimethylaminopyridine. This reaction includes O-acylation and Fries type rearrangement of O-enol acyl group toward adjacent carbon atom. This method is also extended to the preparation of 3-acyl-4-hydroxy-2-pyrones, 2-acyl-3-hydroxy-2-cyclohexen-1-ones and 5-acyl-2,2-dimethyl-1,3-dioxane-4,6-diones.