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Vanadium-catalysed enantioselective sulfoxidations: rational design of biocatalytic and biomimetic systems

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Abstract

Approaches to the rational design of vanadium-based biocatalytic and biomimetic model systems as catalysts for enantioselective oxidations are reviewed. Incorporation of vanadate ion into the active site of phytase (E.C. 3.1.3.8), which in vivo mediates the hydrolysis of phosphate esters, afforded a relatively stable and inexpensive semi-synthetic peroxidase. It catalysed the enantioselective oxidation of prochiral sulfides with H2O2 affording the S-sulfoxide, e.g., in 68% ee at 100% conversion for thioanisole. Amongst the transition metal oxoanions that are known to be potent inhibitors of phosphatases, only vanadate resulted in a semi-synthetic peroxidase, when incorporated into phytase. In a biomimetic approach, vanadium complexes of chiral Schiff's base complexes were encapsulated in the super cages of a hydrophobic zeolite Y. Unfortunately, these ship-in-a-bottle complexes afforded only racemic sulfoxide in the catalytic oxidation of thioanisole with H2O2.

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Authors and Affiliations

  1. Laboratory of Organic Chemistry and Catalysis, Delft University of Technology, Julianalaan 136, 2628 BL, Delft, The Netherlands

    Fred van de Velde, Isabel W.C.E. Arends & Roger A. Sheldon

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  1. Fred van de Velde
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  2. Isabel W.C.E. Arends
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  3. Roger A. Sheldon
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van de Velde, F., Arends, I.W. & Sheldon, R.A. Vanadium-catalysed enantioselective sulfoxidations: rational design of biocatalytic and biomimetic systems. Topics in Catalysis 13, 259–265 (2000). https://doi.org/10.1023/A:1009094619249

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