Indium-Mediated 2-Oxonia Cope Rearrangement of 1,4-Dienols to 1,3-Dienols

[Image: see text] 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 produc...

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Autores principales: Capel, Natalie J., Lindley, Martin R., Pritchard, Gareth J., Kimber, Marc C.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6648455/
https://www.ncbi.nlm.nih.gov/pubmed/31459359
http://dx.doi.org/10.1021/acsomega.8b03118
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author Capel, Natalie J.
Lindley, Martin R.
Pritchard, Gareth J.
Kimber, Marc C.
author_facet Capel, Natalie J.
Lindley, Martin R.
Pritchard, Gareth J.
Kimber, Marc C.
author_sort Capel, Natalie J.
collection PubMed
description [Image: see text] 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.
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spelling pubmed-66484552019-08-27 Indium-Mediated 2-Oxonia Cope Rearrangement of 1,4-Dienols to 1,3-Dienols Capel, Natalie J. Lindley, Martin R. Pritchard, Gareth J. Kimber, Marc C. ACS Omega [Image: see text] 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. American Chemical Society 2019-01-09 /pmc/articles/PMC6648455/ /pubmed/31459359 http://dx.doi.org/10.1021/acsomega.8b03118 Text en Copyright © 2019 American Chemical Society This is an open access article published under an ACS AuthorChoice License (http://pubs.acs.org/page/policy/authorchoice_termsofuse.html) , which permits copying and redistribution of the article or any adaptations for non-commercial purposes.
spellingShingle Capel, Natalie J.
Lindley, Martin R.
Pritchard, Gareth J.
Kimber, Marc C.
Indium-Mediated 2-Oxonia Cope Rearrangement of 1,4-Dienols to 1,3-Dienols
title Indium-Mediated 2-Oxonia Cope Rearrangement of 1,4-Dienols to 1,3-Dienols
title_full Indium-Mediated 2-Oxonia Cope Rearrangement of 1,4-Dienols to 1,3-Dienols
title_fullStr Indium-Mediated 2-Oxonia Cope Rearrangement of 1,4-Dienols to 1,3-Dienols
title_full_unstemmed Indium-Mediated 2-Oxonia Cope Rearrangement of 1,4-Dienols to 1,3-Dienols
title_short Indium-Mediated 2-Oxonia Cope Rearrangement of 1,4-Dienols to 1,3-Dienols
title_sort indium-mediated 2-oxonia cope rearrangement of 1,4-dienols to 1,3-dienols
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6648455/
https://www.ncbi.nlm.nih.gov/pubmed/31459359
http://dx.doi.org/10.1021/acsomega.8b03118
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