FeCl(2)-Mediated Rearrangement of Allylic Alcohols

[Image: see text] A mild, one-pot procedure to produce 3-substituted allylic alcohols from α,β-unsaturated ketones is described. The addition of an organolithium nucleophile produces a tertiary allylic alcohol as an intermediate, which undergoes a 1,3-OH-migration assisted by FeCl(2). The proposed m...

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Autores principales: Oppong-Quaicoe, Anita A., DeBoef, Brenton
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2019
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6648291/
https://www.ncbi.nlm.nih.gov/pubmed/31459755
http://dx.doi.org/10.1021/acsomega.9b00163
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author Oppong-Quaicoe, Anita A.
DeBoef, Brenton
author_facet Oppong-Quaicoe, Anita A.
DeBoef, Brenton
author_sort Oppong-Quaicoe, Anita A.
collection PubMed
description [Image: see text] A mild, one-pot procedure to produce 3-substituted allylic alcohols from α,β-unsaturated ketones is described. The addition of an organolithium nucleophile produces a tertiary allylic alcohol as an intermediate, which undergoes a 1,3-OH-migration assisted by FeCl(2). The proposed mechanism indicates that a syn-facial migration occurs for the major product. Yields as high as 98% for the one-pot reaction are reported.
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spelling pubmed-66482912019-08-27 FeCl(2)-Mediated Rearrangement of Allylic Alcohols Oppong-Quaicoe, Anita A. DeBoef, Brenton ACS Omega [Image: see text] A mild, one-pot procedure to produce 3-substituted allylic alcohols from α,β-unsaturated ketones is described. The addition of an organolithium nucleophile produces a tertiary allylic alcohol as an intermediate, which undergoes a 1,3-OH-migration assisted by FeCl(2). The proposed mechanism indicates that a syn-facial migration occurs for the major product. Yields as high as 98% for the one-pot reaction are reported. American Chemical Society 2019-03-29 /pmc/articles/PMC6648291/ /pubmed/31459755 http://dx.doi.org/10.1021/acsomega.9b00163 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 Oppong-Quaicoe, Anita A.
DeBoef, Brenton
FeCl(2)-Mediated Rearrangement of Allylic Alcohols
title FeCl(2)-Mediated Rearrangement of Allylic Alcohols
title_full FeCl(2)-Mediated Rearrangement of Allylic Alcohols
title_fullStr FeCl(2)-Mediated Rearrangement of Allylic Alcohols
title_full_unstemmed FeCl(2)-Mediated Rearrangement of Allylic Alcohols
title_short FeCl(2)-Mediated Rearrangement of Allylic Alcohols
title_sort fecl(2)-mediated rearrangement of allylic alcohols
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6648291/
https://www.ncbi.nlm.nih.gov/pubmed/31459755
http://dx.doi.org/10.1021/acsomega.9b00163
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