The influence of fluorine in asymmetric catalysis

Abstract

All domains of chemistry are increasingly impacted by organofluorine molecules, often favorably. In asymmetric synthesis of fluorinated compounds, significant achievements are the result of extensive research efforts toward appropriate experimental conditions rather than of the rationalization of fluorine effects. Most of the time, the influence of fluorine is inspected retrospectively. When elaborating a synthetic plan, the question should not be only when and how to introduce fluorine but also how to use the effects of fluorine for a desirable result. The subtle effects of fluorine atom(s) on the course of asymmetric reactions are outlined in this tutorial review. We present some selected examples of asymmetric reactions that involve fluorinated components either as reactants, catalysts, solvents or additives, and a comparative study of the stereochemical outcomes with reactions carried out in the presence of non-fluorinated analogues.