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

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journal contribution
posted on 04.01.2016, 00:00 by Kenichi Hiramatsu, Takashi Honjo, Vivek Rauniyar, F. Dean Toste
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).