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

Research output: Contribution to journal › Article › peer-review

7 Citations (Scopus)

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.

Original language	English
Article number	76
Pages (from-to)	648-652
Number of pages	5
Journal	Beilstein Journal of Organic Chemistry
Volume	7
DOIs	https://doi.org/10.3762/bjoc.7.76
Publication status	Published - 2011 May 20

Keywords

Alkylation
Gold catalysis
Leaving group
Silyl enol ether
Substitution reaction

ASJC Scopus subject areas

Organic Chemistry

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title = "Gold-catalyzed alkylation of silyl enol ethers with ortho-alkynylbenzoic acid esters",

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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