REACTIONS OF AMINO-SUBSTITUTED CYCLODEXTRINS WITH 2-ARYLPROPANOIC ACID-DERIVATIVES

Reactions of 6(A)-amino-6(A)-deoxy-beta-cyclodextrin and )-amino-3(A)- deoxy-(2(A)S,3(A)S)-beta-cyclodextrin with the 3-nitrophenyl esters of 2-phenylpropanoic acid and Ibuprofen occur with only low diastereosel ectivity, to afford the corresponding arylpropanamido-substituted cycl odextrins. These amides are also formed by decarboxylation of correspo nding 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 tempera ture, but becomes dissociated from the cavity as the temperature is in creased.