Ene diiodo acetals: Stereoselective synthesis of ene hydroxy acetals. Handy access to non conjugated dienals

Article abstract of DOI:10.1016/S0040-4020(98)83009-3

After halogen-metal exchange reaction followed by condensation with carbonyl compounds, ene diiodo acetal 1 allow the stereoselective synthesis of ene hydroxy acetals 2 with Z configuration, in a two step procedure. Moreover, after dehydration, the intermediate diene acetals 3-4, via an appropriated hydrolysis procedure, lead to pure non conjugated dienals 5.