Gold-catalyzed intermolecular coupling of sulfonylacetylene with allyl ethers: [3,3]- and [1,3]-rearrangements

Gold-catalyzed intermolecular couplings of sulfonylacetylenes with allyl ethers are reported. A cooperative polarization of alkynes both by a gold catalyst and a sulfonyl substituent resulted in an efficient intermolecular tandem carboalkoxylation. Reactions of linear allyl ethers are consistent wit...

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Detalles Bibliográficos
Autores principales: Jun, Jungho, Yeom, Hyu-Suk, An, Jun-Hyun, Shin, Seunghoon
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2013
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3778381/
https://www.ncbi.nlm.nih.gov/pubmed/24062834
http://dx.doi.org/10.3762/bjoc.9.198
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author Jun, Jungho
Yeom, Hyu-Suk
An, Jun-Hyun
Shin, Seunghoon
author_facet Jun, Jungho
Yeom, Hyu-Suk
An, Jun-Hyun
Shin, Seunghoon
author_sort Jun, Jungho
collection PubMed
description Gold-catalyzed intermolecular couplings of sulfonylacetylenes with allyl ethers are reported. A cooperative polarization of alkynes both by a gold catalyst and a sulfonyl substituent resulted in an efficient intermolecular tandem carboalkoxylation. Reactions of linear allyl ethers are consistent with the [3,3]-sigmatropic rearrangement mechanism, while those of branched allyl ethers provided [3,3]- and [1,3]-rearrangement products through the formation of a tight ion–dipole pair.
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spelling pubmed-37783812013-09-23 Gold-catalyzed intermolecular coupling of sulfonylacetylene with allyl ethers: [3,3]- and [1,3]-rearrangements Jun, Jungho Yeom, Hyu-Suk An, Jun-Hyun Shin, Seunghoon Beilstein J Org Chem Full Research Paper Gold-catalyzed intermolecular couplings of sulfonylacetylenes with allyl ethers are reported. A cooperative polarization of alkynes both by a gold catalyst and a sulfonyl substituent resulted in an efficient intermolecular tandem carboalkoxylation. Reactions of linear allyl ethers are consistent with the [3,3]-sigmatropic rearrangement mechanism, while those of branched allyl ethers provided [3,3]- and [1,3]-rearrangement products through the formation of a tight ion–dipole pair. Beilstein-Institut 2013-08-22 /pmc/articles/PMC3778381/ /pubmed/24062834 http://dx.doi.org/10.3762/bjoc.9.198 Text en Copyright © 2013, Jun 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
Jun, Jungho
Yeom, Hyu-Suk
An, Jun-Hyun
Shin, Seunghoon
Gold-catalyzed intermolecular coupling of sulfonylacetylene with allyl ethers: [3,3]- and [1,3]-rearrangements
title Gold-catalyzed intermolecular coupling of sulfonylacetylene with allyl ethers: [3,3]- and [1,3]-rearrangements
title_full Gold-catalyzed intermolecular coupling of sulfonylacetylene with allyl ethers: [3,3]- and [1,3]-rearrangements
title_fullStr Gold-catalyzed intermolecular coupling of sulfonylacetylene with allyl ethers: [3,3]- and [1,3]-rearrangements
title_full_unstemmed Gold-catalyzed intermolecular coupling of sulfonylacetylene with allyl ethers: [3,3]- and [1,3]-rearrangements
title_short Gold-catalyzed intermolecular coupling of sulfonylacetylene with allyl ethers: [3,3]- and [1,3]-rearrangements
title_sort gold-catalyzed intermolecular coupling of sulfonylacetylene with allyl ethers: [3,3]- and [1,3]-rearrangements
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3778381/
https://www.ncbi.nlm.nih.gov/pubmed/24062834
http://dx.doi.org/10.3762/bjoc.9.198
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