Water-promoted organic reactions. aldol reaction of silyl enol ethers with carbonyl compounds under atmospheric pressure and neutral conditions.

✍ Scribed by Andre´ Lubineau; Elsa Meyer

• Publisher: Elsevier Science
• Year: 1988
• Tongue: French
• Weight: 359 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)89795-7

✦ Synopsis

As a consequence of the hydrophobic effect, the reaction between silyl enol ethers and aldehydes are shown to proceed without a catalyst in aqueous solution and neutral conditions providing crossed-aldol products with a 2Y~ selectivity, as under pressure, that is the reverse in comparison with the acid catalysed reaction. with a,lI-unsaturated aldehydes, 1,2-and 1,4-addition were observed, whereas with a,lI-unsaturated ketones, only 1,4-addition occurred.