Synthetic utility of a fluorine-facilitated Claisen rearrangement: a novel synthetic method for 2, 4-alkadienoic acids using 2, 2, 2-trifluoroethyl phenyl sulfoxide.
A novel synthetic method for 2, 4-alkadienoic acids from allylic alcohols and 2, 2, 2- trifluoroethyl phenyl sulfoxide is described which involves the in situ Claisen rearrangement facilitated by the fluorine. This method was applied to the stereocontrolled synthesis of pellitorine, a natural insecticide.
