Stereoselective Synthesis of Mechanically Planar Chiral Rotaxanes

Abstract

Chiral interlocked molecules in which the mechanical bond provides the sole stereogenic unit are typically produced with no control over the mechanical stereochemistry. Here we report a stereoselective approach to mechanically planar chiral rotaxanes in up to 98:2 d.r. using a readily available α-amino acid-derived azide. Symmetrization of the covalent stereocenter yields a rotaxane in which the mechanical bond provides the only stereogenic element.

Keywords: CuAAC; chirality; rotaxane; stereoselective synthesis; supramolecular chemistry.