Aldehyde-catalyzed epoxidation of unactivated alkenes with aqueous hydrogen peroxide

Triandafillidi, Ierasia and Kokotou, Maroula G Kokotou and Lotter, Dominik and Sparr, Christof and Kokotos, Christoforos G. (2021) Aldehyde-catalyzed epoxidation of unactivated alkenes with aqueous hydrogen peroxide. Chemical Science, 12 (30). pp. 10191-10196.

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Official URL: https://edoc.unibas.ch/85737/

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The organocatalytic epoxidation of unactivated alkenes using aqueous hydrogen peroxide provides various indispensable products and intermediates in a sustainable manner. While formyl functionalities typically undergo irreversible oxidations when activating an oxidant, an atropisomeric two-axis aldehyde capable of catalytic turnover was identified for high-yielding epoxidations of cyclic and acyclic alkenes. The relative configuration of the stereogenic axes of the catalyst and the resulting proximity of the aldehyde and backbone residues resulted in high catalytic efficiencies. Mechanistic studies support a non-radical alkene oxidation by an aldehyde-derived dioxirane intermediate generated from hydrogen peroxide through the Payne and Criegee intermediates.
Faculties and Departments:05 Faculty of Science > Departement Chemie > Chemie > Organische Chemie (Sparr)
UniBasel Contributors:Sparr, Christof
Item Type:Article, refereed
Article Subtype:Research Article
Publisher:The Royal Society of Chemistry
Note:Publication type according to Uni Basel Research Database: Journal article
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Last Modified:19 Dec 2021 12:44
Deposited On:19 Dec 2021 12:44

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