Stereoselective Formation of Functionalized 2-Aryl-tetrahydrofurans from Aromatic Aldehydes via Intramolecular 1,3-Dipolar Cycloadditions (INOC and IOOC)

Abstract α-Allyloxyaldoximes 8, formed by the reduction of β-nitrostyrenes 5 with SnCl2-2H2O in the presence of an unsaturated alcohol, undergo either thermally induced intramolecular oxime olefin cycloaddition (IOOC) to bicyclic isoxazolidines 7, with stereospecific introduction of three stereocenters, or nitrile oxide olefin cycloadditions (INOC) to bicyclic isoxazolines 6. This provides an entry into functionalized tetrahydrofurans and tetrahydropyrans.