Omega submission revision 2.pdf (3.39 MB)
Indium-mediated 2-oxonia cope rearrangement of 1,4-dienols to 1,3-dienols
journal contribution
posted on 2019-01-30, 16:00 authored by Natalie J. Capel, Martin Lindley, Gareth PritchardGareth Pritchard, Marc KimberMarc KimberAn 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 OmegaVolume
4Issue
1Pages
785 - 792Citation
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 SocietyVersion
- 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
2019Notes
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
2470-1343Publisher version
Language
- en