Catalytic Enantioselective Synthesis of Inherently Chiral Calix[4]arenes via Sequential Povarov Reaction and Aromatizations.

Inherently chiral calix[4]arenes represent a unique type of chiral molecules with significant applications, yet their catalytic enantioselective synthesis remains largely underexplored. We report herein the catalytic enantioselective synthesis of inherently chiral calix[4]arenes through the sequential organocatalyzed enantioselective Povarov reaction and aromatizations. The chiral phosphoric acid catalyzed three-component Povarov reaction involving amino group-substituted calix[4]arenes, aldehydes and (di)enamides desymmetrized the prochiral calix[4]arene substrates, which was followed by various aromatization methods, resulting in a diverse array of novel quinoline-containing calix[4]arenes with good yields and high enantioselectivities (up to 75 % yield, 99 % ee).

Kinetic resolution of substituted amido[2.2]paracyclophanes via asymmetric electrophilic amination.

Planar chiral [2.2]paracyclophane derivatives are a type of structurally intriguing and practically useful chiral molecules, which have found a range of important applications in the field of asymmetric catalysis and material science. However, access to enantioenriched [2.

Asymmetric synthesis of planar-chiral macrocycles organocatalyzed enantioselective macrocyclization.

A novel enantioselective macrocyclization method has been developed for the asymmetric synthesis of planar-chiral macrocycles through chiral phosphoric acid-catalyzed intramolecular addition of the hydroxy group with the allenamide moiety. A series of planar-chiral macrocycles bearing various ring sizes (18-member to 22-member) and various functional groups were generated with good to high enantioselectivities.