Synthesis of\nInherently Chiral Homo-heteracalixaromatics

There\nis a resurgence of research interest in inherently\nchiral\ncalixarenes and heteracalixaromatics. However, the examples of macrocyclic\nring-expanded homocalixarenes and heterocalixaromatics of inherent\nchirality are not known. Here we report an efficient method to construct\ninherently chiral N<sub>2</sub>,O<sub>2</sub>-linked homo-heteracalixaromatics\nfrom reductive amination reactions between bis-aldehydes and aliphatic\ndiamines. Examples of post-macrocyclization derivatization were also\ndemonstrated. Enantiomers were obtained from resolution and did not\nundergo racemization at an elevated temperature. This study provides\na new strategy to design novel and functional inherently chiral macrocycles\nthat have potential applications in supramolecular chemistry.