Skip to main content
SpringerLink
Log in

MECHANICAL STEREOCHEMISTRY

Chirality makes a move

  • News & Views
  • Published:

From Nature Chemistry

View current issue Submit your manuscript

Interlocked molecules can exhibit chiral stereogenic elements that are not found in covalently bound systems. Now, the shuttling of the ring in a [2]rotaxane has been shown to result in enantiomeric co-conformations that selectively bind chiral guests.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1
Fig. 2: Examples of recently recognized co-conformational stereogenic units exhibited by rotaxanes and catenanes that have yet to be synthetically realized6.

References

  1. Gal, J. Nat. Chem. 9, 604–605 (2017).

    Article  CAS  Google Scholar 

  2. Corra, S. et al. J. Am. Chem. Soc. 141, jacs.9b00941 (2019).

    Article  Google Scholar 

  3. Mislow, K. & Siegel, J. J. Am. Chem. Soc. 106, 3319–3328 (1984).

    Article  CAS  Google Scholar 

  4. Eliel, E., Wilen, S. & Mander, L. Stereochemistry of Organic Compounds (Wiley, 1994).

  5. Bruns, C. J. & Stoddart, J. F. The Nature of the Mechanical Bond: From Molecules to Machines (Wiley, 2016).

  6. Jamieson, E. M. G., Modicom, F. & Goldup, S. M. Chem. Soc. Rev. 47, 5266–5311 (2018).

    Article  CAS  Google Scholar 

  7. Schill, G. Catenanes, Rotaxanes and Knots (Academic Press, 1971).

  8. Hirose, K. et al. Symmetry 10, 20 (2018).

    Article  Google Scholar 

  9. Jinks, M. A. et al. Angew. Chem. Int. Ed. 57, 14806–14810 (2018).

    Article  CAS  Google Scholar 

  10. Mochizuki, Y., Ikeyatsu, K., Mutoh, Y., Hosoya, S. & Saito, S. Org. Lett. 19, 4347–4350 (2017).

    Article  CAS  Google Scholar 

  11. Quack, M. Angew. Chem. Int. Ed. 41, 4618–4630 (2002).

    Article  CAS  Google Scholar 

  12. Wolf, C. & Bentley, K. W. Chem. Soc. Rev. 42, 5408–24 (2013).

    Article  CAS  Google Scholar 

  13. Shabbir, S. H., Regan, C. J. & Anslyn, E. V. Proc. Natl Acad. Sci. 106, 10487–10492 (2009).

    Article  CAS  Google Scholar 

  14. Herrera, B. T., Pilicer, S. L., Anslyn, E. V., Joyce, L. A. & Wolf, C. J. Am. Chem. Soc. 140, 10385–10401 (2018).

    Article  CAS  Google Scholar 

  15. Jinks, M. A. et al. Angew. Chem. Int. Ed. 57, 14806–14810 (2018).

    Article  CAS  Google Scholar 

  16. Cakmak, Y., Erbas-Cakmak, S. & Leigh, D. A. J. Am. Chem. Soc. 138, 1749–1751 (2016).

    Article  CAS  Google Scholar 

  17. Alvarez-Pérez, M., Goldup, S. M., Leigh, D. A. & Slawin, A. M. Z. J. Am. Chem. Soc. 130, 1836–1838 (2008).

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, University of Southampton, Southampton, UK

    Ellen M. G. Jamieson & Stephen M. Goldup

Authors
  1. Ellen M. G. Jamieson
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Stephen M. Goldup
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Stephen M. Goldup.

Additional information

Twitter: @sgoldup

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Jamieson, E.M.G., Goldup, S.M. Chirality makes a move. Nat. Chem. 11, 765–767 (2019). https://doi.org/10.1038/s41557-019-0320-z

Download citation

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1038/s41557-019-0320-z

  • Springer Nature Limited

This article is cited by

Search

Navigation