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A General Synthesis of Bis‐α‐acyloxy‐1,4‐ and ‐1,5‐diketones Through Catalytic Oxidative Opening of Acylated THF and THP Diols
Author(s) -
Piccialli Vincenzo,
D'Errico Stefano,
Borbone Nicola,
Oliviero Giorgia,
Centore Roberto,
Zaccaria Sabrina
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201554
Subject(s) - chemistry , regioselectivity , tetrahydropyran , catalysis , ruthenium , pyridine , osmium , pincer movement , oxidative phosphorylation , medicinal chemistry , organic chemistry , stereochemistry , ring (chemistry) , biochemistry
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.