Imidazolidinone Nitroxides as Catalysts in the Aerobic Oxidation of Alcohols, en Route to Atroposelective Oxidative Desymmetrization.

New chiral nitroxides based on the imidazolidin-4-one skeleton, and the corresponding hydroxylamines, were prepd. from cyclic nitrones by a straightforward reaction sequence. They were evaluated as catalysts in the aerobic oxidn. of benzyl alc. using different co-catalysts. Both the imidazolidinone nitroxides and hydroxylamines were shown to catalyze the reaction, with the ring substituent having an effect depending on the co-catalytic system. In some cases, rapid oxidn. to benzaldehyde was accomplished at room temp. under an oxygen atm. Moreover, atroposelective desymmetrization was achieved during the aerobic oxidn. of a diol catalyzed by an enantiopure imidazolidinone nitroxide. Finally, the electrochem. behavior of the new hydroxylamines and nitroxides was investigated by cyclic voltammetry, which gave insights into the obsd. catalytic properties. [on SciFinder(R)]

Références

Titre
Imidazolidinone Nitroxides as Catalysts in the Aerobic Oxidation of Alcohols, en Route to Atroposelective Oxidative Desymmetrization.
Type de publication
Article de revue
Année de publication
2014
Revue
Eur. J. Org. Chem.
Volume
2014
Pagination
4884–4896
ISSN
1099-0690
Soumis le 12 avril 2018