Chiral 2 + 3 Keto-Enamine Pseudocyclophanes Derived from 1,3,5-Triformylphloroglucinol

The reactions of 1,3,5-triformyl­phloro­glucinol with (1<i>R</i>,2<i>R</i>)-1,2-diamino­cyclo­hexane, (1<i>R</i>,2<i>R</i>)-1,2-diphenyl­ethylene­diamine, or (<i>R</i>)-2,2′-diamino-1,1′-binaphthyl result in the formation of enantiopure [2 + 3] keto-enamine condensation products, in contrast to analogous reactions of 1,3,5-triformylbenzene, where [4 + 6] Schiff base cages are formed. The X-ray crystal structure of the diamino­cyclohexane 2 + 3 derivative as well as modeled structures of other compounds of this type show cyclophane-like molecules with close contact between the phloroglucinol rings. Density Functional Theory (DFT) calculations confirm that there is a sizable π–π interaction between these rings influencing the conformation of these molecules