Asymmetric Dearomative Fluorination with Novel Phase-transfer Catalysts

摘要

Because fluorine atom and carbon-fluorine bond show unique features, the biological properties of organic compounds can be modulated without significant change in size by incorporation of fluorine atom(s). Thus, efficient and selective fluorination reaction is highly valuable in pharmaceutical and agrochemical sciences. Recently, we developed asymmetric fluorination of allyl amides catalyzed by novel dianionic phase transfer catalyst 1. In this reaction, the carboxylate catalyst forms an ionic pair with cationic Selectfluor, and hydrogen bond interaction between the catalyst carboxylate and the amide group of the substrate is extremely important for high asymmetric induction. We expected that other hydrogen bond donors would act as a directing group in the fluorination reaction.