Electrofluorination of chiral substituted phenylacetic acid derivatives

Abstract

Several recent works on the syntheses of chiral fluorinated organic molecules [P. Bravo and G. Resnati, Tetrahedron Asymmetry, 1 (1990) 661, and references therein] show that stereoselective introduction of this halogen remains an interesting challenge. In this communication, we wish to describe diastereoselective fluorination at benzylic position via an anodic process [Preliminary note: S. Chebli, R. Faure, L. Kaboré, E. Laurent and B. Marquet, Tetrahedron Letters, 31 (1990) 3137]: ▪ The paper will include: • discussion about the efficiency of the inductor group R*, • determination of the absolute configuration of the fluorinated carbon using 19F NMR data of these compounds compared to spectra of esters derived from the unsubstituted acid of known configuration [C. Beguin, S. Hamman, L. Kaboré, E. Laurent and B. Marquet, J. Fluorine Chem., in press], • considerations about the nature of the induction.