title: Enantioselective Synthesis of Fluoro-Dihydroquinazolones and -Benzooxazinones by Fluorination-Initiated Asymmetric Cyclization Reactions.
abstract: 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).
authors.affiliation: Department of Chemistry, University of California Berkeley, California 94720, United States; Department of Medicinal Chemistry, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University, Chiyoda-ku, Tokyo 101-0062, Japan.
authors.forename: Kenichi
authors.initials: K
authors.lastname: Hiramatsu
authors.affiliation: Department of Chemistry, University of California Berkeley, California 94720, United States.
authors.forename: Takashi
authors.initials: T
authors.lastname: Honjo
authors.affiliation: Department of Chemistry, University of California Berkeley, California 94720, United States.
authors.forename: Vivek
authors.initials: V
authors.lastname: Rauniyar
authors.affiliation: Department of Chemistry, University of California Berkeley, California 94720, United States.
authors.forename: F Dean
authors.initials: FD
authors.lastname: Toste
keywords: asymmetric synthesis; chiral anion; cyclization; fluorination; phase-transfer catalyst