A comparative study of the Au-catalyzed cyclization of hydroxy-substituted allylic alcohols and ethers

The Au(I)-catalyzed cyclization of hydroxyallylic ethers to form tetrahydropyrans is reported. Employing (acetonitrile)[(o-biphenyl)di-tert-butylphosphine]gold(I) hexafluoroantimonate, the cyclization reactions were complete within minutes to hours, depending on the substrate. The reaction progress...

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Detalles Bibliográficos
Autores principales: Biannic, Berenger, Ghebreghiorgis, Thomas, Aponick, Aaron
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2011
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3135158/
https://www.ncbi.nlm.nih.gov/pubmed/21804875
http://dx.doi.org/10.3762/bjoc.7.91
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author Biannic, Berenger
Ghebreghiorgis, Thomas
Aponick, Aaron
author_facet Biannic, Berenger
Ghebreghiorgis, Thomas
Aponick, Aaron
author_sort Biannic, Berenger
collection PubMed
description The Au(I)-catalyzed cyclization of hydroxyallylic ethers to form tetrahydropyrans is reported. Employing (acetonitrile)[(o-biphenyl)di-tert-butylphosphine]gold(I) hexafluoroantimonate, the cyclization reactions were complete within minutes to hours, depending on the substrate. The reaction progress was monitored by GC, and comparisons between substrates demonstrate that reactions of allylic alcohols are faster than the corresponding ethers. Additionally, it is reported that Reaxa QuadraPure(TM) MPA is an efficient scavenging reagent that halts the reaction progress.
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spelling pubmed-31351582011-07-29 A comparative study of the Au-catalyzed cyclization of hydroxy-substituted allylic alcohols and ethers Biannic, Berenger Ghebreghiorgis, Thomas Aponick, Aaron Beilstein J Org Chem Full Research Paper The Au(I)-catalyzed cyclization of hydroxyallylic ethers to form tetrahydropyrans is reported. Employing (acetonitrile)[(o-biphenyl)di-tert-butylphosphine]gold(I) hexafluoroantimonate, the cyclization reactions were complete within minutes to hours, depending on the substrate. The reaction progress was monitored by GC, and comparisons between substrates demonstrate that reactions of allylic alcohols are faster than the corresponding ethers. Additionally, it is reported that Reaxa QuadraPure(TM) MPA is an efficient scavenging reagent that halts the reaction progress. Beilstein-Institut 2011-06-14 /pmc/articles/PMC3135158/ /pubmed/21804875 http://dx.doi.org/10.3762/bjoc.7.91 Text en Copyright © 2011, Biannic et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Biannic, Berenger
Ghebreghiorgis, Thomas
Aponick, Aaron
A comparative study of the Au-catalyzed cyclization of hydroxy-substituted allylic alcohols and ethers
title A comparative study of the Au-catalyzed cyclization of hydroxy-substituted allylic alcohols and ethers
title_full A comparative study of the Au-catalyzed cyclization of hydroxy-substituted allylic alcohols and ethers
title_fullStr A comparative study of the Au-catalyzed cyclization of hydroxy-substituted allylic alcohols and ethers
title_full_unstemmed A comparative study of the Au-catalyzed cyclization of hydroxy-substituted allylic alcohols and ethers
title_short A comparative study of the Au-catalyzed cyclization of hydroxy-substituted allylic alcohols and ethers
title_sort comparative study of the au-catalyzed cyclization of hydroxy-substituted allylic alcohols and ethers
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3135158/
https://www.ncbi.nlm.nih.gov/pubmed/21804875
http://dx.doi.org/10.3762/bjoc.7.91
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