Preparation and Stereoselectivity of 1,3-Dipolar Cycloaddition of D-Glucose-Derived Nitrones to N-Arylmaleimides

Article abstract of DOI:10.1007/BF00814148

Nitrones 2 derived from D-glucose oxime and benzaldehydes without employing any protection of hydroxyl group were isolated in pure state.The 1,3-dipolar cycloaddition of 2 to N-arylmaleimides gave predominantly the anti isoxazolidines 3 and was rationalized by Z/E isomerization of N-glycosylnitrones 2.The structure and steric configuration of the products have been assigned on the basis of 1H- and 13C-NMR spectroscopy.AM1 calculations of the nitrones and MM2 calculations of the adducts were performed. - Keywords. 1,3-Dipolar cycloaddition of chiral nitrones; D-Glucose-derived nitrones; Stereoselectivity of 1,3-dipolar cycloaddition; AM1 Calculations.