Journal
TETRAHEDRON
Volume 68, Issue 51, Pages 10530-10535Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2012.08.078
Keywords
Selenium; Hydrogen peroxide; Catalysis; On water reaction; Diols
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Funding
- M.I.U.R. (Ministero Italiano Universita e Ricerca), National Projects PRIN2007 Fondazione Cassa di Risparmio: Project 'Processi ecosostenibili per la produzione e l'analisi di molecole di interesse farmaceutico' [2012.0114.021]
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The selenium atom of the selenocysteine plays a crucial role in the reduction of peroxides. Herein we showed that, in the absence of a thiol cofactor, the same aminoacid efficiently catalyzed the dihydroxylation of carbon-carbon double bonds leading to the stereoselective formation of 1,2-diols at room temperature and in on water conditions. Alternatively, in the presence of methanol, the corresponding beta-methoxyalcohol can be prepared. The stereoselectivity of the reaction will be discussed and NMR evidences of the actual catalyst are here reported. (C) 2012 Elsevier Ltd. All rights reserved.
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