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Org. Biomol. Chem., 2004, 2, 2403 - 2407, DOI: 10.1039/B407937J
The RuO4-catalysed dihydroxylation, ketohydroxylation and mono oxidation—novel oxidation reactions for the synthesis of diols and
-hydroxy ketonesBernd Plietker and Meike Niggemann
-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 -hydroxy ketones with both predictable regioselectivity and absolute configuration.
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