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 me
α-methylenation of lactones and esters zinc bromide-catalysed phenylthiomethylation of o-silylated enolates
✍ Scribed by Ian Paterson; Ian Fleming
- Publisher
- Elsevier Science
- Year
- 1979
- Tongue
- French
- Weight
- 144 KB
- Volume
- 20
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
The a-methylene unit of a-methylene lactones 2.
📜 SIMILAR VOLUMES
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.
## SwmnarY ZnBr2-catalysed phenylthloalkylatlon of ketene bls(trlmethylsllyl)acetals, obtalned from carboxyllc acids, with appropriate a-chlorosulphldes can be used to prepare y-and 6lactones O-Sllylated enolate chemistry has recently produced new and improved methods for forming carbon-carbon bon