Enantioselective Synthesis of Fluoro–Dihydroquinazolones and −Benzooxazinones by Fluorination-Initiated Asymmetric Cyclization Reactions

Stereoselective synthesis of two
fluorine-bearing drug-like scaffolds,
dihydroquinazolone and benzooxazinone, has been accomplished through
asymmetric fluorocyclization reactions initiated by the fluorination
process. The reaction employs double axially chiral anionic phase-transfer
catalysts to achieve high diastereo- and enantioselectivities, and
a wide range of fluorine-containing dihydroquinazolones were obtained
(>20:1 dr, up to 98% ee).