Reactions of amino-substituted cyclodextrins with 2-arylpropanoic acid derivatives

Abstract

<jats:p> Reactions of 6A-amino-6A-deoxy-β-cyclodextrin and 3A-amino-3A-deoxy-(2AS,3AS)-β-cyclodextrin with the 3-nitrophenyl esters of 2-phenylpropanoic acid and Ibuprofen occur with only low diastereoselectivity, to afford the corresponding arylpropanamido-substituted cyclodextrins. These amides are also formed by decarboxylation of corresponding malonates, again with only low diastereoselectivity. The n.m.r. spectra of the amido-substituted cyclodextrins indicate that the aryl substituent is included within the cyclodextrin annulus at low temperature, but becomes dissociated from the cavity as the temperature is increased.</jats:p>