Synthesis and Asymmetric Recognition of Chiral Calixarenes

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Calixarenes act as novel host molecules not only for metal ions but also for charged and uncharged organic molecules. The purpose of the present research was to design such calixarenes that can asymmetrically recognized optically-active organic molecules. The research strategies are (1) introduction of optically-active substituents and (ii) asymmetric arrangement of substituents on the calixarene ring. Chiral calixarenes synthesized on the basis of strategy (1) showed the selective binding toward chiral guest molecules, which was easily detected by circular dichroism.Strategy (2) involves a new idea in which more than three different substituents are arranged in (R) direction or (S) direction. however, if ring inversion takes place, these optical isomers can racemize. we thus developed a new synthetic method by which inversion of the calix[4]arene ring could he suppressed. We finally succeeded in optical resolution by using a chiral-packing HPLC column. This is the first example for optical resolution of ring-originating, chiral calix[4]arenes.Several attempts to use these chiral calixarenes for asymmetric molecular recognition were reported.