Chiral Crystals from Dynamic Combinatorial Libraries of Achiral Macrocyclic Imines

Dynamic
combinatorial chemistry (DCC) was initially introduced
as a means to solve problems of effective synthesis of complex compounds
in solution. It benefits from the use of reversible reactions to connect
simple building blocks under thermodynamic control. We present an
application of DCC to generate structurally diverse crystalline complexes
of macrocyclic imines, some of which crystallized as chiral crystals,
despite the use of achiral substrates only. Features of imine complexes
such as easy synthesis of building blocks and a high tendency to crystallize
make them good candidates for studying the relationship between molecular
structure and crystallinity.