A General Synthesis of Bis?螃窿?acyloxy??1, 4??and??1, 5??diketones Through Catalytic Oxidative Opening of Acylated THF and THP Diols

V Piccialli, S D'Errico, N Borbone…

Index: Piccialli, Vincenzo; D'Errico, Stefano; Borbone, Nicola; Oliviero, Giorgia; Centore, Roberto; Zaccaria, Sabrina European Journal of Organic Chemistry, 2013 , # 9 p. 1781 - 1789

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Abstract

Abstract The first general synthesis of bis-α-acyloxy-1, 4-and-1, 5-diketones has been accomplished in a catalytic oxidative opening of bis-acylated THF and THP (tetrahydropyran) diols, which were synthesised by osmium-or ruthenium-catalysed oxidative cyclisation of 1, 5-and 1, 6-dienes. The overall sequence corresponds to the regioselective double ketoacyloxylation of the starting diene. The synthesised bis-α- ...