The RuO4-catalysed dihydroxylation, ketohydroxylation and mono oxidation--novel oxidation reactions for the synthesis of diols and alpha-hydroxy ketones.
Alpha-hydroxy ketones are versatile intermediates for the synthesis of complex molecular architectures and subunits of a variety of natural products. Different approaches towards the synthesis of this important functional group combination have been elaborated. The present article summarises our research on the field of RuO4-catalysed oxidations of alkenes that resulted in the development of the first RuO4-catalysed ketohydroxylation of olefins. Mechanistic investigations of both dihydroxylation and ketohydroxylation led to the discovery of the first regioselective catalytic mono oxidation of vic-diols, which was applied in a two-step sequence of asymmetric dihydroxylation and regioselective mono oxidation to furnish enantiopure alpha-hydroxy ketones with both predictable regioselectivity and absolute configuration.
Plietker
Bernd
B
Organische Chemie II, Fachbereich Chemie, Universitat Dortmund, Otto-Hahn-Str. 6, D-44221, Dortmund, Germany. plietker@pop.uni-dortmund.de
Niggemann
Meike
M
D002384:Catalysis; D006018:Glycols / Q000138:chemical synthesis*; D006900:Hydroxylation; D007659:Ketones / Q000138:chemical synthesis*; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D017975:Ruthenium Compounds / Q000737:chemistry*
D006018:Glycols; D007659:Ketones; D017975:Ruthenium Compounds; C027646:ruthenium tetraoxide