Macrocyclic structures and cages are of interest in many fields of chemistry whose efficient synthesis is often a challenging target. In the case of C2 symmetrical pseudopeptides, efficient [n+m] macrocyclization processes can be obtained by preorganizing the open-chain precursos in a folded conformation. Although in some cases structural and configurational preorganization can be obtained, the interaction of those precursors with anions, either organic or inorganic can be used to direct the process to the formation of the desired product. Anions can act both as kinetic and thermodinamic templates. A change in the anion present can also be used to modify the nature of the final compound obtained. Thus, it is possible to obtain [2+2] or [3+3] macrocyclizations as the major product by a proper selection of the conditions. The use of C3 open-chain pseudopeptidic precursors, on the other hand, opens the way for the efficient preparation of pseudopeptidic cages.

Supramolecular preorganization induced by anions for the easy and efficient access to pseudopeptidic macrocyclic structures and cages

243rd National Meeting (2012)

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