title: Proline as Lewis base catalyst: diastereoselective synthesis of isoxazoline-N-oxide through [3 + 2] cycloaddition.
abstract: A catalytic cascade synthesis of isoxazoline-N-oxide was developed through proline-catalyzed nitroalkene activation. A large substrate scope was obtained with good to excellent yields. Mechanistic studies revealed intramolecular cyclization as the rate-determining step, giving only trans isomers in all cases.
authors: C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, West Virginia 26506, USA.
authors: Haifeng
authors: H
authors: Duan
authors: Xiaohua
authors: X
authors: Sun
authors: Wenyan
authors: W
authors: Liao
authors: Jeffrey L
authors: JL
authors: Petersen
authors: Xiaodong
authors: X
authors: Shi
mesh_terms: D002384:Catalysis; D003497:Cyclic N-Oxides / Q000737:chemistry*; D003500:Cyclization; D004952:Esters / Q000737:chemistry; D007555:Isoxazoles / Q000737:chemistry*; D011392:Proline / Q000737:chemistry*; D013237:Stereoisomerism; D013379:Substrate Specificity; D014753:Vinyl Compounds / Q000737:chemistry
chemical_list: D003497:Cyclic N-Oxides; D004952:Esters; D007555:Isoxazoles; D014753:Vinyl Compounds; D011392:Proline