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

Research output: Contribution to journalArticle

6 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 contributionSilylenol ether functionalization, III. Regioselective acylation of trimethylsilylenol ethers with 2-alkoxy-1,3-dioxolanes. Synthesis of α- and γ-protected dicarbonyl compounds
Original languageGerman
Pages (from-to)587-595
Number of pages9
JournalMonatshefte für Chemie Chemical Monthly
Volume115
Issue number5
DOIs
StatePublished - May 1 1984

Keywords

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

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