Stereoselective Synthesis of Mechanically Planar Chiral Rotaxanes. Issue 45 (17th October 2018)

• Record Type: Journal Article
• Authors: Jinks, Michael A.; de Juan, Alberto; Denis, Mathieu; Fletcher, Catherine J.; Galli, Marzia; Jamieson, Ellen M. G.; Modicom, Florian; Zhang, Zhihui; Goldup, Stephen M.
• Is Part Of: Angewandte Chemie international edition. Volume 57:Issue 45(2018)
• Page Start: 14806
• Page End: 14810
• Publication Date: 2018-10-17
• Subjects: chirality -- CuAAC -- rotaxane -- stereoselective synthesis -- supramolecular chemistry; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201808990
• Languages: English
• ISSNs: 1433-7851

Abstract

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.