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Title: Indium-mediated 2-oxonia cope rearrangement of 1,4-dienols to 1,3-dienols
Authors: Capel, Natalie J.
Lindley, Martin R.
Pritchard, Gareth J.
Kimber, Marc C.
Keywords: Addition reaction
Carbonyl compounds (organic)
Physical and chemical processes
Issue Date: 2019
Publisher: © American Chemical Society
Citation: CAPEL, N.J. ... et al, 2019. Indium-mediated 2-oxonia cope rearrangement of 1,4-dienols to 1,3-dienols. ACS Omega, 4 (1), pp.785-792.
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.
Description: 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.
Sponsor: We gratefully acknowledge the financial support from Loughborough University (studentship for NJC).
Version: Accepted for publication
DOI: 10.1021/acsomega.8b03118
URI: https://dspace.lboro.ac.uk/2134/36715
Publisher Link: https://doi.org/10.1021/acsomega.8b03118
Appears in Collections:Published Articles (Sport, Exercise and Health Sciences)
Published Articles (Chemistry)

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