Synthesis and characterisation of macrocyclic diamino chiral crown ethers

A benign and efficient synthesis of chiral macrocyclic 'aza-crown' ethers of varying ring size is reported. The synthesis involves a Schiff base condensation of ether linked dialdehydes of varying chain length and (1R,2R)-(-)-1,2-diaminocyclohexane under mild conditions to yield the macrocycles, which are subsequently reduced to yield the diamino analogues.