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 |
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Original language | German |
Pages (from-to) | 587-595 |
Number of pages | 9 |
Journal | Monatshefte für Chemie Chemical Monthly |
Volume | 115 |
Issue number | 5 |
DOIs | |
State | Published - May 1 1984 |
Keywords
- Dicarbonyl compounds, α- and γ-protected
- Synthesis, with trimethylsilylenol ethers and cyclic ortho esters