title: An improved procedure to prepare 3-methyl-4-nitroalkylenethylisoxazoles and their reaction under catalytic enantioselective Michael addition with nitromethane.
abstract: Herein, we describe a short synthesis of 3-methyl-4-nitro-5-alkylethenyl isoxazoles and their reactivity as Michael acceptors. The title compounds reacted with nitromethane under phase-transfer catalysis to provide highly enantioenriched adducts (up to 93% ee) which were then converted to the corresponding γ-nitroacids.
authors.affiliation: Centre for Synthesis and Chemical Biology (CSCB), Department of Pharmaceutical and Medicinal Chemistry, Royal College of Surgeons in Ireland, 123 St. Stephen's Green, Dublin 2, Ireland. madamo@rcsi.ie mariamoccia@rcsi.ie.
authors.forename: Maria
authors.initials: M
authors.lastname: Moccia
authors.forename: Robert J
authors.initials: RJ
authors.lastname: Wells
authors.forename: Mauro F A
authors.initials: MF
authors.lastname: Adamo
mesh_terms: D002384:Catalysis; D007555:Isoxazoles / Q000138:chemical synthesis* / Q000737:chemistry; D008697:Methane / Q000031:analogs & derivatives* / Q000737:chemistry; D015394:Molecular Structure; D009595:Nitroparaffins / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D007555:Isoxazoles; D009595:Nitroparaffins; D008697:Methane; C008640:nitromethane