The acid accelerated ruthenium-catalysed dihydroxylation. Scope and limitations

Organic & Biomolecular Chemistry Pub Date: 2004-03-24 DOI: 10.1039/B316546A

Abstract

Recently, we discovered a significant rate acceleration in RuO4-catalysed dihydroxylations of olefins by addition of Br?nsted-acids resulting in a reduction of the catalyst loading to only 0.5 mol%. The present paper gives a full account on the optimisation protocol that led to the discovery of the beneficial influence of protic acids. A strong focus is set on the detailed description of the influence of different reaction parameters on both reactivity and selectivity. In the second part an intense investigation of scope and limitations will be presented. The results provided in this manuscript might lead to a deeper understanding of competing processes that influence the selectivity in RuO4-catalysed dihydroxylations.

Graphical abstract: The acid accelerated ruthenium-catalysed dihydroxylation. Scope and limitations
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