Cucurbit[8]uril recognition of rapidly interconverting diastereomers

Abstract

<div><p>The diastereoselectivity of Cucurbit[8]uril (CB[8]) binding was probed towards a series of rapidly interconverting diastereomers containing a C_aryl–C_aryl chiral axis and at least one other stereocenter. Relative binding affinities of up to 4.9 were determined when CB[8] interacted with <i>ortho</i>, <i>meta</i>, <i>ortho′</i>-substituted biphenyls bearing a chiral dialkylsulfonium substituent at their <i>meta</i>-position. Diastereoselectivities of up to 2.4-fold were obtained for <i>ortho′</i>-substituted 2-phenylpyridinium derivatives that bear a chiral myrtenyl <i>N</i>-substituent prone to CB[8] binding.</p></div