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

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Adam G. Meyer, Christopher J. Easton, Stephen F. Lincoln and Gregory W. Simpson


Abstract

The 1,3-dipolar cycloaddition of 4-tert-butylbenzonitrile oxide with 6A-acrylamido-6A-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.


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