Dynamic combinatorial libraries of macrocyclic imines and their applications

Abstract

The reversibility of imine formation from amines and carbonyl compounds, such as aldehydes and ketones, allows the generation of dynamic combinatorial libraries (DCLs). By applying templates to these DCLs, members matching these templates can be amplified. Starting from the very same DCLs, the addition of different templates allows the synthesis of different products. The nature of the template alone determines which product is amplified. The template can also protect the imine bond from hydrolysis. Thus, imines can be generated in the presence of water. In mixtures of water and hydrophobic layers, transport has been observed. In contrast to most transport experiments, in which suitable ion carriers have to be added, in the systems described here, the ions act as templates for the formation of their own carriers. © 2013 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.