Diastereoselective cycloadditions of a soluble polymer-supported substituted allyl alcohol derived from Baylis–Hillman reaction with nitrile oxides

A diastereoselective cycloaddition of a soluble polymer-supported Baylis–Hillman adduct with nitrile oxides is described. The reaction has shown to proceed with moderate diastereoselectivity, favoring the syn isomer of the resulting 3,5-substituted isoxazolines. The stereochemistry of the products has been assigned using 1H NMR studies. The structure of one of the diastereomers has been determined by single-crystal X-ray crystallographic analysis.

Figure optionsDownload as PowerPoint slide