Synthesis of new optically pure isoxazolines via 1,3-dipolar cycloaddition of nitrile oxides with allyl esters derived from eugenol

Abstract

1,3-dipolar cycloaddition of arylnitrile oxides with allyl ester prepared from eugenol afforded new chiral isoxazolines in good yields. The chemical structure of this compounds was characterized by ¹H NMR,¹³C NMR, 2D NMR and TOF-MS analysis. All the cycloadducts were obtained through a regiospecific and stereospecific pathway and all cases, only one isomer was isolated, as established by unambiguous NMR analysis