Portal de Periódicos da CAPES

Templating Irreversible Covalent Macrocyclization by Using Anions

2013; Wiley; Volume: 19; Issue: 11 Linguagem: Inglês

10.1002/chem.201204306

1521-3765

Evgeny A. Kataev, Grigory V. Kolesnikov, René Arnold, H.V. Lavrov, Victor N. Khrustalev,

Supramolecular Chemistry and Complexes

Abstract Inorganic anions were used as templates in the reaction between a diamine and an activated diacid to form macrocyclic amides. The reaction conditions were found to perform the macrocyclization sufficiently slow to observe a template effect. A number of analytical methods were used to clarify the reaction mechanisms and to show that the structure of the intermediate plays a decisive role in determining the product distribution. For the macrocyclization under kinetic control, it was shown that the amount of a template, the conformational rigidity of building blocks, and the anion affinities of reaction components and intermediates are important parameters that one should take into consideration to achieve high yields.