Unprecedented in situ oxidative ring cleavage of isoxazolidines: diastereoselective transformation of nitronic acids and derivatives into 3-hydroxymethyl 4-nitro tetrahydrofurans and pyrrolidines.
[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.
Roger
Pierre-Yves
PY
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.
Durand
Anne-Catherine
AC
Rodriguez
Jean
J
Dulcère
Jean-Pierre
JP
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
D005663:Furans; D007555:Isoxazoles; D009574:Nitro Compounds; D011759:Pyrrolidines