title: Organocatalytic asymmetric one-pot sequential conjugate addition/dearomative fluorination: synthesis of chiral fluorinated isoxazol-5(4H)-ones.
abstract: A facile one-pot sequential conjugate addition/dearomative fluorination transformation of isoxazol-5(4H)-ones with nitroolefins and N-fluorobenzenesulfonimide (NFSI) has been developed. By using a bifunctional chiral tertiary amino-thiourea catalyst, a series of chiral fluorinated isoxazol-5(4H)-ones containing one fluorine-substituted quarternary stereocenter were obtained in high yields with high enantio- and diastereoselectivities. Further transformation of adducts could afford isoxazolidin-5-one derivatives with three contiguous stereocenters.
authors.affiliation: Department of Chemistry, Tianjin University, Tianjin, 300072, PR of China.
authors.forename: Wen-Ting
authors.initials: WT
authors.lastname: Meng
authors.forename: Yan
authors.initials: Y
authors.lastname: Zheng
authors.forename: Jing
authors.initials: J
authors.lastname: Nie
authors.forename: Heng-Ying
authors.initials: HY
authors.lastname: Xiong
authors.forename: Jun-An
authors.initials: JA
authors.lastname: Ma
mesh_terms: D002384:Catalysis; D054879:Halogenation; D007555:Isoxazoles / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013449:Sulfonamides / Q000138:chemical synthesis* / Q000737:chemistry*; D013890:Thiourea / Q000737:chemistry*; D000096926:Benzenesulfonamides
chemical_list: D007555:Isoxazoles; D013449:Sulfonamides; D013890:Thiourea; C523711:N-fluorobenzenesulfonimide; D000096926:Benzenesulfonamides