Stereoselective Synthesis of Mechanically Planar Chiral Rotaxanes. Issue 45 (17th October 2018) - Jinks, Michael A.
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. Abstract : Taking (stereo)control of the mechanical bond : A stereoselective approach to mechanically planar chiral rotaxanes in up to 98:2 d.r . using a readily available α‐amino acid‐derived azide is reported. Symmetrization of the covalent stereocenter yields a rotaxane in which the mechanical bond provides the only stereogenic element in excellent enantiopurity.