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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Format: | Article |
Language: | English |
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Beilstein-Institut
2011-05-01
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Series: | Beilstein Journal of Organic Chemistry |
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Online Access: | https://doi.org/10.3762/bjoc.7.76 |
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author | Haruo Aikawa Tetsuro Kaneko Naoki Asao Yoshinori Yamamoto |
author_facet | Haruo Aikawa Tetsuro Kaneko Naoki Asao Yoshinori Yamamoto |
author_sort | Haruo Aikawa |
collection | DOAJ |
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. |
first_indexed | 2024-12-13T23:17:50Z |
format | Article |
id | doaj.art-79d0e7fc19b04d109173d112b04cd82a |
institution | Directory Open Access Journal |
issn | 1860-5397 |
language | English |
last_indexed | 2024-12-13T23:17:50Z |
publishDate | 2011-05-01 |
publisher | Beilstein-Institut |
record_format | Article |
series | Beilstein Journal of Organic Chemistry |
spelling | doaj.art-79d0e7fc19b04d109173d112b04cd82a2022-12-21T23:27:53ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972011-05-017164865210.3762/bjoc.7.761860-5397-7-76Gold-catalyzed alkylation of silyl enol ethers with ortho-alkynylbenzoic acid estersHaruo Aikawa0Tetsuro Kaneko1Naoki Asao2Yoshinori Yamamoto3Department of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, JapanDepartment of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, JapanDepartment of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, JapanDepartment of Chemistry, Graduate School of Science, Tohoku University, Sendai 980-8578, JapanUnprecedented 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.https://doi.org/10.3762/bjoc.7.76alkylationgold catalysisleaving groupsilyl enol ethersubstitution reaction |
spellingShingle | Haruo Aikawa Tetsuro Kaneko Naoki Asao Yoshinori Yamamoto Gold-catalyzed alkylation of silyl enol ethers with ortho-alkynylbenzoic acid esters Beilstein Journal of Organic Chemistry alkylation gold catalysis leaving group silyl enol ether substitution reaction |
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 | alkylation gold catalysis leaving group silyl enol ether substitution reaction |
url | https://doi.org/10.3762/bjoc.7.76 |
work_keys_str_mv | AT haruoaikawa goldcatalyzedalkylationofsilylenoletherswithorthoalkynylbenzoicacidesters AT tetsurokaneko goldcatalyzedalkylationofsilylenoletherswithorthoalkynylbenzoicacidesters AT naokiasao goldcatalyzedalkylationofsilylenoletherswithorthoalkynylbenzoicacidesters AT yoshinoriyamamoto goldcatalyzedalkylationofsilylenoletherswithorthoalkynylbenzoicacidesters |