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:	Schools > Chemistry
Subjects:	Q Science > QD Chemistry
Uncontrolled Keywords:	Selenium; Hydrogen peroxide; Catalysis; On water reaction; Diols
Publisher:	Elsevier
ISSN:	0040-4020
Related URLs:	Publisher
Last Modified:	24 Oct 2022 10:50
URI:	https://orca.cardiff.ac.uk/id/eprint/46127

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