Enantioselective synthesis of 2-fluoro carboxylic acids from Trichloromethyl carbinols: an efficient approach to chiral fluorine introduction into insect sex pheromones

Abstract Chiral syntheses of 2-fluoro carboxylic acids were achieved (ee ≥ 92%, yield 50–60%) by stereoselective conversion (with inversion of configuration) of optically active trichloromethyl carbinols to fluoroacids with tetrabutylammonium fluoride. Fluorinated pheromone analogs of the European corn borer, Ostrinia nubilalis , and of the beet armyworm, Spodoptera exigua , were synthesized.