Unprecedented selectivity in the formation of large-ring oligoimines from conformationally bistable chiral diamines

reaction: see text] Stereoselective formation of large macrocycles in "click-type" reactions is a current challenge. Chiral macrocycles of differing size and shape (e.g., rectanglimine or loopimine) were selectively obtained by cyclocondensation of terephthalaldehyde or isophthalaldehyde with conformationally bistable chiral diamines derived from trans-1,2-diaminocyclohexane and aromatic dianhydrides. This opens new opportunities for the programmed synthesis of large-ring molecular assemblies.