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Stereoselective selenium catalyzed dihydroxylation and hydroxymethoxylation of alkenes

Santi, Claudio, Di Lorenzo, Rosalia, Tidei, Caterina, Bagnoli, Luana and Wirth, Thomas ORCID: https://orcid.org/0000-0002-8990-0667 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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Abstract

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
Related URLs:
Last Modified: 24 Oct 2022 10:50
URI: https://orca.cardiff.ac.uk/id/eprint/46127

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