Calix[6]arene Threading with Weakly Interacting Tertiary Ammonium Axles: Generation of Chiral Pseudorotaxane Architectures

The TFPB “superweak anion” effectively induces the threading of a scarcely preorganized calix[6]­arene (1) with weakly interacting tertiary ammonium axles (2⁺–3⁺). The pseudorotaxanes (4⁺–5⁺) thus formed show an unexpected chirality due to an unprecedented formation of a threading-induced stereogenic ammonium center.