SYNTHETIC UTILITY OF A FLUORINE-FACILITATED CLAISEN REARRANGEMENT: A NOVEL SYNTHETIC METHOD FOR 2,4-ALKANEDIENOIC ACIDS USING 2,2,2-TRIFLUOROETHYL PHENYL SULFOXIDE

Article abstract of DOI:10.1246/cl.1981.1289

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.