title: Unprecedented in situ oxidative ring cleavage of isoxazolidines: diastereoselective transformation of nitronic acids and derivatives into 3-hydroxymethyl 4-nitro tetrahydrofurans and pyrrolidines.
abstract: [reaction: see text] Nitronic acids undergo an intramolecular 1,3-dipolar cycloaddition to unactivated double bonds, and the resulting isoxazolidines spontaneously evolve by an unprecedented in situ oxidative ring cleavage. The extension of this transformation to silyl nitronates results in a general diastereoselective construction of hydroxymethyl nitro functionalized tetrahydro-furans and -pyrrolidine having up to four consecutive stereogenic centers.
authors.affiliation: Université d'Aix-Marseille III, Laboratoire Symbio, UMR 6178, Centre de St Jérôme, Boîte D 12, Av. Esc. Normandie-Niemen, F-13397 Marseille Cedex 20, France.
authors.forename: Pierre-Yves
authors.initials: PY
authors.lastname: Roger
authors.forename: Anne-Catherine
authors.initials: AC
authors.lastname: Durand
authors.forename: Jean
authors.initials: J
authors.lastname: Rodriguez
authors.forename: Jean-Pierre
authors.initials: JP
authors.lastname: Dulcère
mesh_terms: D003500:Cyclization; D005663:Furans / Q000138:chemical synthesis*; D007555:Isoxazoles / Q000138:chemical synthesis*; D008968:Molecular Conformation; D009574:Nitro Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D010084:Oxidation-Reduction; D011759:Pyrrolidines / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D005663:Furans; D007555:Isoxazoles; D009574:Nitro Compounds; D011759:Pyrrolidines