Substrate- and Reagent-Controlled Electrophilic Asymmetric Fluorinations

In the past twenty years, the development of efficient methods for asymmetric fluorination is one of the most fascinating aspects of modern organofluorine chemistry. Among the many approaches towards the construction of chiral organofluorine compounds containing a fluorine atom bonded directly to a stereogenic center, electrophilic asymmetric fluorination has proven to be particularly effective. In this review, substrate-mediated diastereoselective electrophilic fluorinations for the synthesis of chiral organofluorine compounds is first discussed, followed by chiral reagent-controlled stoichiometric asymmetric electrophilc fluorination of achiral compounds, with emphasis on the developments and applications of neutral chiral N-F agents based on the sultam templates and charged chiral [N-F]+ reagents derived from the fluorinated cinchona alkaloids or the alkaloids/Selectfluor combination.