The first general synthesis of bis-α-acyloxy-1,4- and -1,5-di ketones has been accomplished in a catalytic oxidative open ing 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 ketoacylox-ylation of the starting diene. The synthesised bis-α-acyloxy-1,5-dicarbonyl compounds have been transformed into pyridine-based oxido pincer ligands or pyrazinedimethanol substances, leading to the discovery of unprecedented aromatisation routes.

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

PICCIALLI, VINCENZO;D'ERRICO, STEFANO;BORBONE, NICOLA;OLIVIERO, GIORGIA;CENTORE, ROBERTO;ZACCARIA, SABRINA
2013

Abstract

The first general synthesis of bis-α-acyloxy-1,4- and -1,5-di ketones has been accomplished in a catalytic oxidative open ing 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 ketoacylox-ylation of the starting diene. The synthesised bis-α-acyloxy-1,5-dicarbonyl compounds have been transformed into pyridine-based oxido pincer ligands or pyrazinedimethanol substances, leading to the discovery of unprecedented aromatisation routes.
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/11588/561392
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