A cyclodextrin to reverse the regioselectivity of nitrile oxide cycloaddition to a terminal alkene

Abstract

The 1,3-dipolar cycloaddition of 4-tert-butylbenzonitrile oxide with 6 ^A -acrylamido-6 ^A -deoxy-β-cyclodextrin in aqueous solution favours formation of the 4-substituted isoxazoline, in contrast to the normal predominance of the 5-substituted regioisomer from reactions of monosubstituted alkenes.