Stereoselective Synthesis of Mechanically Planar Chiral Rotaxanes

Michael A. Jinks, Alberto de Juan, Mathieu Denis, Catherine J. Fletcher, Marzia Galli, Ellen M.G. Jamieson, Florian Modicom, Zhihui Zhang, Stephen M. Goldup*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

46 Citations (Scopus)


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.

Original languageEnglish
Pages (from-to)14806-14810
Number of pages5
JournalAngewandte Chemie - International Edition
Issue number45
Publication statusPublished - 5 Nov 2018

Bibliographical note

Funding Information:
S.M.G. thanks the European Research Council (Consolidator Grant Agreement no. 724987), EPSRC (EP/L016621/1) and Leverhulme Trust (ORPG-2733) for funding and the Royal Society for a Research Fellowship. M.D. and M.G. thank the EPSRC for a Doctoral Prize. E.M.G.J. and F.M. thank the EPSRC for financial support (EP/L505067/1). Z.Z. thanks the China Scholarship Council for a Scholarship. The authors thank Reach Separations for assistance with analytical CSP-HPLC.

Publisher Copyright:
© 2018 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim


  • chirality
  • CuAAC
  • rotaxane
  • stereoselective synthesis
  • supramolecular chemistry

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry


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