On the preparation and rearrangement of some vinylic sulphoxides

Abstract

The condensation of methyl benzenesulphinylacetate 1 with a series of aldehydes has been explored using different catalysts. With zinc chloride, the enolate of 1 produces the conjugated ester directly. A base-catalysed rearrangement of these conjugated esters to the corresponding γ-hydroxy unsaturated ester can be effected. Alternatively, the use of magnesium methoxide as catalyst during the condensation of the aldehydes with the reagent 1 produces these hydroxy esters directly.