862379-50-8Relevant articles and documents
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
, p. 1781 - 1789 (2013/04/10)
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-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. The first general synthesis of bis-α-acyloxy-1,4- and -1,5-diketones is reported. The process features the catalytic oxidative opening of bis-acylated THF and THP diols, which were synthesised by the transition-metal-mediated oxidative cyclisation of 1,5- and 1,6-dienes. The 1,5-diketone products were cyclised to give pyridinedimethanol derivatives. New aromatisation modes have been disclosed. Copyright