A New Family of Chiral Binaphthyl-Derived Cyclophane Receptors: Complexation of Pyranosides


  • This work was supported by the Schweizerische Nationalfonds zur Förderung der wissenschaftlichen Forschung (Chiral 2) and Hoffmann–La Roche. S. A. thanks the Royal Society, London, for a European Science Exchange Programme Postdoctoral Fellowship and Trinity College, Cambridge, for a Research Fellowship. We thank Dipl.-Chem. Jens Cuntze for the NMR titrations.

  • Dedicated to Professor Dr. Manfred Regitz on occasion of his 60th birthday


original image

Even in the presence of a protic solvent (up to 20% v/v CD3OD) the optically active cyclophane tetraanion in (R,R,R,R)-1 binds to carbohydrates such as 1-O-octyl-β-D-glycopyranoside. In addition, neutral cyclophanes with similarly highly organized cavities are suitable binders in chloroform. The macrocycles are synthesized by Glaser–Hay coupling of novel chiral diethynylated 1,1'-binaphthyl monomers.