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MECHANICAL STEREOCHEMISTRY

Chirality makes a move

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.

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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

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Correspondence to Stephen M. Goldup.

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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

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