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Indium-mediated 2-oxonia cope rearrangement of 1,4-dienols to 1,3-dienols

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posted on 30.01.2019 by Natalie J. Capel, Martin Lindley, Gareth Pritchard, Marc Kimber
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.

Funding

We gratefully acknowledge the financial support from Loughborough University (studentship for NJC).

History

School

  • Sport, Exercise and Health Sciences

Published in

ACS Omega

Volume

4

Issue

1

Pages

785 - 792

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.

Publisher

© American Chemical Society

Version

AM (Accepted Manuscript)

Publisher statement

This work is made available according to the conditions of the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0) licence. Full details of this licence are available at: https://creativecommons.org/licenses/by-nc-nd/4.0/

Publication date

2019

Notes

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.

eISSN

2470-1343

Language

en

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