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

Haruo Aikawa; Tetsuro Kaneko; Naoki Asao; Yoshinori Yamamoto

doi:10.3762/bjoc.7.76

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

Haruo Aikawa, Tetsuro Kaneko, Naoki Asao, Yoshinori Yamamoto

研究成果: Article › 査読

8 被引用数 (Scopus)

抄録

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.

本文言語	English
論文番号	76
ページ（範囲）	648-652
ページ数	5
ジャーナル	Beilstein Journal of Organic Chemistry
巻	7
DOI	https://doi.org/10.3762/bjoc.7.76
出版ステータス	Published - 2011 5月 20

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有機化学

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abstract = "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.",

keywords = "Alkylation, Gold catalysis, Leaving group, Silyl enol ether, Substitution reaction",

author = "Haruo Aikawa and Tetsuro Kaneko and Naoki Asao and Yoshinori Yamamoto",

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language = "English",

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AU - Aikawa, Haruo

AU - Kaneko, Tetsuro

AU - Asao, Naoki

AU - Yamamoto, Yoshinori

PY - 2011/5/20

Y1 - 2011/5/20

N2 - 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.

AB - 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.

KW - Alkylation

KW - Gold catalysis

KW - Leaving group

KW - Silyl enol ether

KW - Substitution reaction

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JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

SN - 1860-5397

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

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