FLUCYC · Asymmetric Fluorocyclisations

Fluorinated oxygen- or nitrogen-containing heterocycles (lactones, lactams, pyrrolidines and tetrahydrofurans) are important compounds with application in the pharmaceutical and agrochemical industry or as performance compounds in material science. Enantioenriched F-heterocycles with the fluorine substituent on a stereogenic centre are of particular interest but are not easy to access using known protocols. The aim of this proposal is to develop an asymmetric route (including a catalytic variant) to fluorinated heterocycles from prochiral starting materials relying on a fluorocyclisation as the key step. The project builds on literature and data from our laboratory showing that activated and allylsilanes are amenable to fluorocyclisation. Two approaches will be considered to access enantioenriched fluorocyclised heterocycles, based on the use of both novel chiral N-F reagents and well-documented fluorinated cinchona alkaloid derivatives.