Enantioselective Organocatalytic Fluorination-Induced Wagner-Meerwein Rearrangement

摘要

Despite the fact that only 21 fJuorinated molecules are known to be biosynthesized, it is notable that about 20-25 % of all modern pharmaceuticals and agrochemicals incorporate at least one fluorine atom. Nevertheless, the practice of introducing fluorine atoms into bioactive compounds is rather recent, as the first synthetic fluorinated drug, namely 5-fluorouracil, was synthesized as late as in 1957 . Ever since, the research aimed at incorporating fluorine atoms into small organic molecules has attracted and intrigued synthetic organic chemists.Yet, despite the importance of fluorine, carbon-fluorine bond formation remains a challenge. Performing this task in concert with bringing chirality into the target molecule, and doing so with only a catalytic quantity of the enantioinducing reagent is of even greater practical importance.