Silylenolether-Funktionalisierung, 3. Mitt. Regioselektive Acylierung von Trimethylsilylenolethern mit 2-Alkoxy-1,3-dioxolanen - Synthese von α- und γ-geschützten Dicarbonylverbindungen

Eyup Akgün; Ulf Pindur

doi:10.1007/BF00799167

Silylenolether-Funktionalisierung, 3. Mitt. Regioselektive Acylierung von Trimethylsilylenolethern mit 2-Alkoxy-1,3-dioxolanen - Synthese von α- und γ-geschützten Dicarbonylverbindungen

Translated title of the contribution: Silylenol ether functionalization, III. Regioselective acylation of trimethylsilylenol ethers with 2-alkoxy-1,3-dioxolanes. Synthesis of α- and γ-protected dicarbonyl compounds

Eyup Akgün
, Ulf Pindur

Medicinal Chemistry

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

8 Scopus citations

Abstract

Acylation of silylenol ethers 1 and 9 yield with 2-alkoxy-2-alkyl(or aryl)-1,3-dioxolanes 5 in a simple way by zinc dichloride-diethyl ether-catalysis regioselectively the α- and γ-protected dicarbonyl derivatives 6, 7, and 10. The enhanced reactivity of the cyclic orthoesters 5 in this reaction is discussed in comparison with acyclic reagents. The yield is influenced by steric effects at the reaction center.

Translated title of the contribution	Silylenol ether functionalization, III. Regioselective acylation of trimethylsilylenol ethers with 2-alkoxy-1,3-dioxolanes. Synthesis of α- and γ-protected dicarbonyl compounds
Original language	German
Pages (from-to)	587-595
Number of pages	9
Journal	Monatshefte für Chemie Chemical Monthly
Volume	115
Issue number	5
DOIs	https://doi.org/10.1007/BF00799167
State	Published - May 1984

Keywords

Dicarbonyl compounds, α- and γ-protected
Synthesis, with trimethylsilylenol ethers and cyclic ortho esters

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10.1007/BF00799167

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Silylenolether-Funktionalisierung, 3. Mitt. Regioselektive Acylierung von Trimethylsilylenolethern mit 2-Alkoxy-1,3-dioxolanen - Synthese von α- und γ-geschützten Dicarbonylverbindungen. / Akgün, Eyup; Pindur, Ulf.
In: Monatshefte für Chemie Chemical Monthly, Vol. 115, No. 5, 05.1984, p. 587-595.

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

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abstract = "Acylation of silylenol ethers 1 and 9 yield with 2-alkoxy-2-alkyl(or aryl)-1,3-dioxolanes 5 in a simple way by zinc dichloride-diethyl ether-catalysis regioselectively the α- and γ-protected dicarbonyl derivatives 6, 7, and 10. The enhanced reactivity of the cyclic orthoesters 5 in this reaction is discussed in comparison with acyclic reagents. The yield is influenced by steric effects at the reaction center.",

keywords = "Dicarbonyl compounds, α- and γ-protected, Synthesis, with trimethylsilylenol ethers and cyclic ortho esters",

author = "Eyup Akg{\"u}n and Ulf Pindur",

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AU - Akgün, Eyup

AU - Pindur, Ulf

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N2 - Acylation of silylenol ethers 1 and 9 yield with 2-alkoxy-2-alkyl(or aryl)-1,3-dioxolanes 5 in a simple way by zinc dichloride-diethyl ether-catalysis regioselectively the α- and γ-protected dicarbonyl derivatives 6, 7, and 10. The enhanced reactivity of the cyclic orthoesters 5 in this reaction is discussed in comparison with acyclic reagents. The yield is influenced by steric effects at the reaction center.

AB - Acylation of silylenol ethers 1 and 9 yield with 2-alkoxy-2-alkyl(or aryl)-1,3-dioxolanes 5 in a simple way by zinc dichloride-diethyl ether-catalysis regioselectively the α- and γ-protected dicarbonyl derivatives 6, 7, and 10. The enhanced reactivity of the cyclic orthoesters 5 in this reaction is discussed in comparison with acyclic reagents. The yield is influenced by steric effects at the reaction center.

KW - Dicarbonyl compounds, α- and γ-protected

KW - Synthesis, with trimethylsilylenol ethers and cyclic ortho esters

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JO - Monatshefte für Chemie Chemical Monthly

JF - Monatshefte für Chemie Chemical Monthly

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ER -

Silylenolether-Funktionalisierung, 3. Mitt. Regioselektive Acylierung von Trimethylsilylenolethern mit 2-Alkoxy-1,3-dioxolanen - Synthese von α- und γ-geschützten Dicarbonylverbindungen

Abstract

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