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Capel, NJ, Lindley, MR, Pritchard, GJ and Kimber, MC (2019) Indium-Mediated 2-Oxonia Cope Rearrangement of 1,4-Dienols to 1,3-Dienols. ACS Omega, 4. 785 -792. ISSN 2470-1343

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Abstract

An indium-mediated isomerization of 1,4-dienols to 1,3-dienols is described. This procedure consists of the addition of pentadienylindium, in a protic solvent, to aldehydes giving the kinetic γ-allylation product in high yields. The subsequent conversion of this γ-allylation product to its thermodynamic 1,3-dienol α-isomer can be achieved by its exposure to indium triflate in the presence of a substoichiometric amount of aldehyde at room temperature. This transformation exhibited moderate to good substrate scope and has been shown to proceed by a 2-oxonia Cope rearrangement.

Item Type: Article
Additional Information: This is the final published version of the article (version of record). It first appeared online via ACS at https://doi.org/10.1021/acsomega.8b03118 - please refer to any applicable terms of use of the publisher. This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
Uncontrolled Keywords: Addition reaction; Carbonyl compounds (organic); Catalysts; Physical and chemical processes
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Natural Sciences > School of Chemical and Physical Sciences
Depositing User: Symplectic
Date Deposited: 25 Mar 2019 12:43
Last Modified: 25 Mar 2019 12:43
URI: https://eprints.keele.ac.uk/id/eprint/6104

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