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α-Alkylation of ketones, esters, and lactones: zinc bromide-catalysed alkylation of o-silylated enolates, a synthesis of (±)-ar-turmerone

✍ Scribed by Ian Paterson

Publisher
Elsevier Science
Year
1979
Tongue
French
Weight
125 KB
Volume
20
Category
Article
ISSN
0040-4039

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✦ Synopsis

O-Silylated ketone enolates can be alkylated regiospecifically with t-alkyl halides in the presence of an equivalent of titanium tetrachloride;

2 for the alkylation of lithium enolates, in general, dialkylation,3 loss of regiospecificity,3 and self-condensation4 are common problems.

Alternative methods 3,5 for the specific alkylation of ketones are best suited for alkylation at the less-substituted side.

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γ-Alkylation of unsaturated ketones and
γ-Alkylation of unsaturated ketones and esters: zinc bromide-catalysed alkylation of O-silylated dienolates
✍ Ian Fleming; John Goldhill; Ian Paterson 📂 Article 📅 1979 🏛 Elsevier Science 🌐 French ⚖ 216 KB

The O-silylated dienolates of unsaturated ketones and esters can be alkylated using zinc bromide catalysis to give predominantly the y-alkylated carbonyl compounds. The substitution pattern of the substrate (11, favours, in certain cases, very high or complete y-selectivity.