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Selective Synthesis of Unsymmetrical Aliphatic Acyloins through Oxidation of Iridium Enolates
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0002-1729-598X
Stockholm University, Faculty of Science, Department of Organic Chemistry.ORCID iD: 0000-0001-9774-0731
Stockholm University, Faculty of Science, Department of Organic Chemistry.
Number of Authors: 32018 (English)In: Chemistry - A European Journal, ISSN 0947-6539, E-ISSN 1521-3765, Vol. 24, no 45, p. 11564-11567Article in journal (Refereed) Published
Abstract [en]

The first method to access unsymmetrical aliphatic acyloins is presented. The method relies on a fast 1,3-hydride shift mediated by an Ir-III complex in allylic alcohols followed by oxidation with TEMPO+. The direct conversion of allylic alcohols into acyloins is achieved in a one-pot procedure. Further functionalization of the C alpha' of the alpha-amino-oxylated ketone products gives access to highly functionalized unsymmetrical aliphatic ketones, which further highlights the utility of this transformation.

Place, publisher, year, edition, pages
2018. Vol. 24, no 45, p. 11564-11567
Keywords [en]
allylic alcohols, hydride shifts, iridium, oxidation, alpha-hydroxy ketones
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:su:diva-160118DOI: 10.1002/chem.201803117ISI: 000441126900008PubMedID: 29928782OAI: oai:DiVA.org:su-160118DiVA, id: diva2:1249060
Available from: 2018-09-18 Created: 2018-09-18 Last updated: 2019-05-08Bibliographically approved

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Sanz-Marco, AmparoMartinez-Erro, SamuelMartín-Matute, Belén
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