Regio- And Diastereo-Selective Formation Of Isoxazoline Derivatives By Lewis Acid Mediated 1,3-Dipolar Cycloaddition Reactions Of Nitrile Oxide

In the presence of magnesium perchlorate, 1,3-dipolar cycloaddition reactions of nitrile oxides to crotonamide bearing 4-benzyl-5,5-dimethyl-1,3-oxazolidin-2-one as the chiral auxiliary proceeded with a regio- and diastereoselective manner to afford the corresponding chiral 2-isoxazoline. The mechanisms underlying the diastereoface selection in the cycloaddition reaction were investigated using the B3LYP/6-31G* level of theory.