Gold-catalyzed alkylation of silyl enol ethers with ortho-alkynylbenzoic acid esters

Unprecedented alkylation of silyl enol ethers has been developed by the use of ortho-alkynylbenzoic acid alkyl esters as alkylating agents in the presence of a gold catalyst. The reaction probably proceeds through the gold-induced in situ construction of leaving groups and subsequent nucleophilic at...

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Detalles Bibliográficos
Autores principales: Aikawa, Haruo, Kaneko, Tetsuro, Asao, Naoki, Yamamoto, Yoshinori
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2011
Materias:
Letter
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3107469/
https://www.ncbi.nlm.nih.gov/pubmed/21647329
http://dx.doi.org/10.3762/bjoc.7.76
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author Aikawa, Haruo
Kaneko, Tetsuro
Asao, Naoki
Yamamoto, Yoshinori
author_facet Aikawa, Haruo
Kaneko, Tetsuro
Asao, Naoki
Yamamoto, Yoshinori
author_sort Aikawa, Haruo
collection PubMed
description Unprecedented alkylation of silyl enol ethers has been developed by the use of ortho-alkynylbenzoic acid alkyl esters as alkylating agents in the presence of a gold catalyst. The reaction probably proceeds through the gold-induced in situ construction of leaving groups and subsequent nucleophilic attack on the silyl enol ethers. The generated leaving compound abstracts a proton to regenerate the silyl enol ether structure.
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spelling pubmed-31074692011-06-06 Gold-catalyzed alkylation of silyl enol ethers with ortho-alkynylbenzoic acid esters Aikawa, Haruo Kaneko, Tetsuro Asao, Naoki Yamamoto, Yoshinori Beilstein J Org Chem Letter Unprecedented alkylation of silyl enol ethers has been developed by the use of ortho-alkynylbenzoic acid alkyl esters as alkylating agents in the presence of a gold catalyst. The reaction probably proceeds through the gold-induced in situ construction of leaving groups and subsequent nucleophilic attack on the silyl enol ethers. The generated leaving compound abstracts a proton to regenerate the silyl enol ether structure. Beilstein-Institut 2011-05-20 /pmc/articles/PMC3107469/ /pubmed/21647329 http://dx.doi.org/10.3762/bjoc.7.76 Text en Copyright © 2011, Aikawa 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 Letter
Aikawa, Haruo
Kaneko, Tetsuro
Asao, Naoki
Yamamoto, Yoshinori
Gold-catalyzed alkylation of silyl enol ethers with ortho-alkynylbenzoic acid esters
title Gold-catalyzed alkylation of silyl enol ethers with ortho-alkynylbenzoic acid esters
title_full Gold-catalyzed alkylation of silyl enol ethers with ortho-alkynylbenzoic acid esters
title_fullStr Gold-catalyzed alkylation of silyl enol ethers with ortho-alkynylbenzoic acid esters
title_full_unstemmed Gold-catalyzed alkylation of silyl enol ethers with ortho-alkynylbenzoic acid esters
title_short Gold-catalyzed alkylation of silyl enol ethers with ortho-alkynylbenzoic acid esters
title_sort gold-catalyzed alkylation of silyl enol ethers with ortho-alkynylbenzoic acid esters
topic Letter
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3107469/
https://www.ncbi.nlm.nih.gov/pubmed/21647329
http://dx.doi.org/10.3762/bjoc.7.76
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