The RuO4-catalysed dihydroxylation, ketohydroxylation and mono oxidation—novel oxidation reactions for the synthesis of diols and α-hydroxy ketones

Bernd Plietker; Meike Niggemann

doi:10.1039/B407937J

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The RuO₄-catalysed dihydroxylation, ketohydroxylation and mono oxidation—novel oxidation reactions for the synthesis of diols and α-hydroxy ketones†

Bernd Plietker*^a and Meike Niggemann^a

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* Corresponding authors

^a Organische Chemie II, Fachbereich Chemie, Universität Dortmund, Otto-Hahn-Str. 6, Dortmund, Germany
E-mail: plietker@pop.uni-dortmund.de
Fax: +49-231-7553884
Tel: +49-231-7554632

Abstract

α-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 α-hydroxy ketones with both predictable regioselectivity and absolute configuration.

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Article information

DOI: https://doi.org/10.1039/B407937J
Article type: Emerging Area
Submitted: 27 May 2004
First published: 05 Aug 2004

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Org. Biomol. Chem., 2004,2, 2403-2407

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The RuO₄-catalysed dihydroxylation, ketohydroxylation and mono oxidation—novel oxidation reactions for the synthesis of diols and α-hydroxy ketones

B. Plietker and M. Niggemann, Org. Biomol. Chem., 2004, 2, 2403 DOI: 10.1039/B407937J

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Organic & Biomolecular Chemistry