N,N-Ethylene-bridged flavinium salts derived from l-valinol: synthesis and catalytic activity in H2O2 oxidations |
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| Authors: | Ji?í ?urek,Hana Dvo?á ková |
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| Affiliation: | a Department of Organic Chemistry, Institute of Chemical Technology, Prague, Technická 5, 166 28 Prague 6, Czech Republic
b Central Laboratories, Institute of Chemical Technology, Prague, Technická 5, 166 28 Prague 6, Czech Republic |
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| Abstract: | Three chiral N1,N10-ethylene-bridged flavinium salts with a stereogenic centre derived from l-valinol are prepared and investigated as oxidation catalysts. These salts efficiently catalyse chemoselective H2O2 oxidation of sulfides to sulfoxides and the oxidation of 3-phenylcyclobutanone to the corresponding lactone at room temperature. The flavinium salts react with hydrogen peroxide to form flavin-10a-hydroperoxide, which is the agent responsible for oxidation of the substrate. |
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| Keywords: | Organocatalysis Oxidation Flavinium salts Hydrogen peroxide |
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