Templating irreversible covalent macrocyclization by using anions.
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.
Institut für Chemie, Technische Universität Chemnitz, Strasse der Nationen, 62, 09111 Chemnitz, Germany. evgeny.kataev@chemie.tu-chemnitz.de
Evgeny A
EA
Kataev
Grigory V
GV
Kolesnikov
Rene
R
Arnold
Herman V
HV
Lavrov
Victor N
VN
Khrustalev