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Chiral cyclotriveratrylene-based molecular cages: Synthesis and molecular recognition properties

The synthesis of cyclotriveratrylene (CTV) – a rigid, bowl-shaped macrocyclic compound consisting of three veratrole units – and its derivatives, as well as the properties of these compounds are reported. Application of this synthon in the preparation of molecular cages is discussed. Special emphasis is put on the synthesis of hemicryptophanes: inherently chiral, covalently bound cage-type molecular receptors with ditopic cavity, consisting of a C 3-symmetrical cyclotriveratrylene scaffold (existing in the P and M configuration) triply connected to another unit. Such cages are prepared in most cases as racemic mixtures resulting from the inherent chirality of CTV. Enantiomerically pure CTV-cages are rare; most typical examples of the synthesis of such derivatives are discussed in detail. Application of such supramolecular structures in chiral recognition is also discussed.