Mild acetalisation of mono and dicarbonyl compounds catalysed by titanium tetrachloride. Facile synthesis of beta-keto enol ethers

The use of TiCl4, as a catalyst for the acetalisation, at room temperature, of carbonyl compounds is reported. Cyclic ketones and cyclic 1,4-diketones easily afford dimethyl acetals, but cyclic 1,3-diketones give beta -keto enol ethers. Additionally, aryl ketones and acyclic ketones failed to react. beta -keto aldehydes can be monoprotected either as beta -keto enol ethers or beta -keto dimethyl acetals depending on the reaction time and catalyst amount. Some mechanistic features are accounted for. (C) 2000 Elsevier Science Ltd. All rights reserved.