title: Highly diastereo- and enantioselective organocatalytic one-pot sequential 1,4-addition/dearomative-fluorination transformation.
abstract: Fluorination: A wide range of nitroolefins and pyrazol-5-ones undergo a sequential 1,4-addition/dearomative-fluorination transformation when treated with a catalytic amount of a tertiary-amine-thiourea compound and the terminal electrophile, N-fluorobenzenesulfonimide, to give fluorinated products in 72-95% yield with up to 99:1 d.r. and 98% ee. Notably, these products contain adjacent tertiary and α-fluoro quaternary stereocenters (see scheme).
authors.affiliation: Department of Chemistry, Tianjin University, Tianjin 300072, PR China.
authors.forename: Feng
authors.initials: F
authors.lastname: Li
authors.forename: Long
authors.initials: L
authors.lastname: Sun
authors.forename: Yuou
authors.initials: Y
authors.lastname: Teng
authors.forename: Peng
authors.initials: P
authors.lastname: Yu
authors.forename: John Cong-Gui
authors.initials: JC
authors.lastname: Zhao
authors.forename: Jun-An
authors.initials: JA
authors.lastname: Ma
mesh_terms: D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D054879:Halogenation; D008968:Molecular Conformation; D011720:Pyrazoles / Q000737:chemistry; D013237:Stereoisomerism; D013449:Sulfonamides / Q000138:chemical synthesis / Q000737:chemistry*; D013890:Thiourea / Q000737:chemistry*; D000096926:Benzenesulfonamides
chemical_list: D000588:Amines; D011720:Pyrazoles; D013449:Sulfonamides; D013890:Thiourea; C523711:N-fluorobenzenesulfonimide; D000096926:Benzenesulfonamides