title: Catalytic Asymmetric Synthesis of Isoxazolines from Silyl Nitronates.
abstract: 1,3-Dipolar cycloadditions of triisopropylsilyl nitronates and 2-alkylacroleins produced isoxazolines bearing a chiral quaternary center in high yields and enantioselectivities with the aid of a chiral oxazaborolidine catalyst. One chiral isoxazoline product was converted to (R)-(+)-Tanikolide in 9 steps in a total yield of 43%.
authors.affiliation: Key Laboratory of Radiopharmaceuticals, College of Chemistry, Beijing Normal University, Beijing 100875, P. R. China.
authors.forename: Xiaoyu
authors.initials: X
authors.lastname: Han
authors.affiliation: Key Laboratory of Radiopharmaceuticals, College of Chemistry, Beijing Normal University, Beijing 100875, P. R. China.
authors.forename: Li
authors.initials: L
authors.lastname: Dong
authors.affiliation: Key Laboratory of Radiopharmaceuticals, College of Chemistry, Beijing Normal University, Beijing 100875, P. R. China.
authors.forename: Caiwei
authors.initials: C
authors.lastname: Geng
authors.affiliation: Key Laboratory of Radiopharmaceuticals, College of Chemistry, Beijing Normal University, Beijing 100875, P. R. China.
authors.forename: Peng
authors.initials: P
authors.lastname: Jiao
mesh_terms: D002384:Catalysis; D018360:Crystallography, X-Ray; D061565:Cycloaddition Reaction; D007555:Isoxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009574:Nitro Compounds / Q000737:chemistry*; D017646:Organosilicon Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D007555:Isoxazoles; D007783:Lactones; D009574:Nitro Compounds; D017646:Organosilicon Compounds; C400156:tanikolide