Synthesis of selectively fluorinated molecules from dimethylsulfoxide, fluoroacetic acid esters and diazomethane

Small, simple and polyfunctionalized fluorine-containing molecules were obtained through simple synthetic sequences, starting from cheap and readily available dimethylsulfoxide and fluorinated acetic acid esters. A comparison between the present results and those obtained when p-tolyl was one of the carbon ligands of sulfur shows a strict consistence in the stereocontrolling behaviour of the sulfoxide group acting as the chiral auxiliary in the two cases. © 1998 Elsevier Science S.A. All rights reserved.