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)

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.

Original languageEnglish
Pages (from-to)14806-14810
Number of pages5
JournalAngewandte Chemie - International Edition
Volume57
Issue number45
DOIs
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

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry

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