Journal
TETRAHEDRON LETTERS
Volume 51, Issue 7, Pages 1083-1086Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2009.12.096
Keywords
Organocatalysis; Oxidation; Flavinium salts; Hydrogen peroxide
Categories
Funding
- Czech Science Foundation [203/07/1246]
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Three chiral N-1,N-10-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. (C) 2009 Elsevier Ltd. All Fights reserved.
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