Phenylthiomethylstannylation of silyl enol ethers and silyl dienol ethers

✍ Scribed by Javed Iqbal

• Publisher: Elsevier Science
• Year: 1989
• Tongue: French
• Weight: 212 KB
• Volume: 30
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)95170-0

✦ Synopsis

Silyl enol ethers (2) react with trihutyl [(phenylthio) chloromethyl] stannane (1) in the presence of Zinc bromide to give B-phenylthiomethylstannyl ketones (3) in good yields. Silyl dienol ethers (4) mainly give products (5) due to y-attack, under these conditions. S-Stannyl Carbonyl compounds have found widespread1 use in organic synthesis owing to their ability to act as masked homoenolate anion equivalent. The utility of Carbon-tin bond in carbon-carbon bond formation has been exploited with remarkable success by transmetallation2 with organ0 lithium reagents or by their activation3 with Lewis acids like TiCl4. Recently a new dimension has heen added to this area of research where a carbon-tin bond can be induced to undergo a carbon-carbon bond formation promoted by free-radical initiators4 or transition metal catalysts5.