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Stereoselective selenium catalyzed dihydroxylation and hydroxymethoxylation of alkenes

Santi, Claudio, Di Lorenzo, Rosalia, Tidei, Caterina, Bagnoli, Luana and Wirth, Thomas 2012. Stereoselective selenium catalyzed dihydroxylation and hydroxymethoxylation of alkenes. Tetrahedron 68 (51) , pp. 10530-10535. 10.1016/j.tet.2012.08.078

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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 β-methoxyalcohol can be prepared. The stereoselectivity of the reaction will be discussed and NMR evidences of the actual catalyst are here reported.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Chemistry
Subjects: Q Science > QD Chemistry
Uncontrolled Keywords: Selenium; Hydrogen peroxide; Catalysis; On water reaction; Diols
Publisher: Elsevier
ISSN: 0040-4020
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Last Modified: 04 Jun 2017 04:53

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