How to synthesize macrocycles efficiently by using virtual combinatorial libraries.
The selection of different diimines 4 a-c by alkaline earth ions from a virtual combinatorial library (VCL) is described. The products were stabilized by reduction to the diamines 6 a-c; this allowed easy analysis. The library can be directed toward different target molecules 6 a-c upon addition of alkaline earth ions with different radii. Competition experiments show the possibility of synthesizing the macrocycles 6 a, 6 b, and 6 c simultaneously when using Mg(2+), Ca(2+), and Ba(2+) as template ions. The scope of this thermodynamically controlled, reversible approach for macrocycle syntheses is illustrated.
Storm
Ole
O
Institut für Organische Chemie Christian-Albrechts-Universität zu Kiel Otto-Hahn-Platz 4, 24098 Kiel, Germany.
Lüning
Ulrich
U
D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D006571:Heterocyclic Compounds / Q000138:chemical synthesis*; D007097:Imines / Q000138:chemical synthesis; D008673:Metals, Alkaline Earth / Q000737:chemistry
D006571:Heterocyclic Compounds; D007097:Imines; D008673:Metals, Alkaline Earth