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Aldehyde-catalyzed epoxidation of unactivated alkenes with aqueous hydrogen peroxide
JournalArticle (Originalarbeit in einer wissenschaftlichen Zeitschrift)
 
ID 4634999
Author(s) Triandafillidi, Ierasia; Kokotou, Maroula G Kokotou; Lotter, Dominik; Sparr, Christof; Kokotos, Christoforos G
Author(s) at UniBasel Sparr, Christof
Year 2021
Title Aldehyde-catalyzed epoxidation of unactivated alkenes with aqueous hydrogen peroxide
Journal Chemical Science
Volume 12
Number 30
Pages / Article-Number 10191-10196
Abstract 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.
Publisher The Royal Society of Chemistry
ISSN/ISBN 1478-6524
edoc-URL https://edoc.unibas.ch/85737/
Full Text on edoc No
Digital Object Identifier DOI 10.1039/d1sc02360h
PubMed ID http://www.ncbi.nlm.nih.gov/pubmed/34377408
ISI-Number WOS:000667708400001
Document type (ISI) Journal Article
 
   

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28/03/2024