Templating irreversible covalent macrocyclization by using anions.

Autor: Kataev EA; Institut für Chemie, Technische Universität Chemnitz, Strasse der Nationen, 62, 09111 Chemnitz, Germany. evgeny.kataev@chemie.tu-chemnitz.de, Kolesnikov GV, Arnold R, Lavrov HV, Khrustalev VN
Jazyk: angličtina
Zdroj: Chemistry (Weinheim an der Bergstrasse, Germany) [Chemistry] 2013 Mar 11; Vol. 19 (11), pp. 3710-4. Date of Electronic Publication: 2013 Jan 31.
DOI: 10.1002/chem.201204306
Abstrakt: 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.
(Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)
Databáze: MEDLINE
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