Twisted Allenyl-Pyridocyclophanes by Templated Cyclooligomerization: Chiral Cavities for Precision Molecular Recognition.

ABSTRACT: We report the palladium-catalyzed one-pot synthesis of enantiopure 20-, 30-, and 40-membered cyclophanes shaped by axially twisted allene units. Under Cs⁺-template, the two smaller macrocycles (2 and 3) are favored over the largest (4). X-ray studies reveal that rac-2 assembles into homochiral helices that pack to form channels, while rac-3 forms racemic dimers. These shape-persistent hosts, with unique chiral 3D cavities, undergo guest-induced conformational switching and (enantio)-selectively bind diols and ammonium cations, including hydroxycarboxylic acids and α-hydroxyammoniums, as evidenced by diagnostic ECD shifts.

SUBMITTER: Alvarez-Garcia J 

PROVIDER: S-EPMC12848741 | biostudies-literature | 2026 Jan

REPOSITORIES: biostudies-literature