WATER-PROMOTED ORGANIC REACTIONS. ALDOL REACTION OF SILYL ENOL ETHERS WITH CARBONYL COMPOUNDS UNDER ATMOSPHERIC PRESSURE AND NEUTRAL CONDITIONS.

Article abstract of DOI:10.1016/S0040-4020(01)89795-7

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 syn selectivity, as under pressure, that is the reverse in comparison with the acid catalysed reaction.With α,β-unsaturated aldehydes, 1,2- and 1,4-addition were observed, whereas with α,β-unsaturated ketones, only 1,4-addition occured.