Imine- and Amine-Type Macrocycles Derived from Chiral Diamines and Aromatic Dialdehydes

The condensation of aromatic dialdehydes with chiral diamines, such as 1,2-trans-diaminocyclohexane, leads to various enantiopure or meso-type macrocyclic Schiff bases, including [2 + 2], [3 + 3], [4 + 4], [6 + 6] and [8 + 8] condensation products. Unlike most cases of macrocycle synthesis, the [3 + 3] macrocycles of this type are sometimes obtained in high yields by direct condensation without a metal template. Macrocycles of other sizes from this family can often be selectively obtained in high yields by a suitable choice of metal template, solvent, or chirality of the building blocks. In particular, the application of a cadmium(II) template results in the expansion of the [2 + 2] macrocycles into giant [6 + 6] and [8 + 8] macrocycles. These imine macrocycles can be reduced to the corresponding macrocyclic amines which can act as hosts for the binding of multiple cations or multiple anions.

Automated summary

Condensation of aromatic dialdehydes with chiral diamines can produce various enantiopure or meso-type macrocyclic Schiff bases. Different sizes of macrocycles can be selectively obtained by choosing suitable metal templates, solvents, or chiral building blocks. These imine macrocycles can be reduced to macrocyclic amines that can act as hosts for binding multiple cations or anions.