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Induction of molecular asymmetry by a remote chiral group
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  • Letter
  • Published: 27 February 1997

Induction of molecular asymmetry by a remote chiral group

  • Patrick Linnane1,
  • Nicholas Magnus1 &
  • Philip Magnus1 

Nature volume 385, pages 799–801 (1997)Cite this article

  • 564 Accesses

  • 42 Citations

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Abstract

Conventional methods of asymmetric synthesis of organic compounds involve the use of either chiral catalysts or stoichiometric amounts of chiral substrates. Invariably, the reacting components must be in close proximity to the entity that introduces chirality1,2. But supramolecular chemistry3–5 has shown that stereochemical information can be transmitted through greater distances than are commonly involved in asymmetric syntheses. Here we show that chiral information can be transmitted with remarkable selectivity through as many as nine achiral connecting atoms to give predominantly one diastereomer of a possible four. This contrasts with the general expectation6 that a decrease in selectivity would result from an increase in the separation of the chirality-inducing substituent and the reaction site. This ability to convey molecular asymmetry over larger distances should provide access to new chiral molecules that would be difficult to make by conventional methods.

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References

  1. Seebach, D., Inwinkelried, R. & Weber, T. in Modern Synthetic Methods Vol. 4 (ed. Scheffold, R.) 125 (Springer, Berlin, 1986).

    Google Scholar 

  2. Morrison, H. (ed.) Asymmetric Synthesis Vols 1–5 (Academic, Orlando, FL, 1986).

  3. Lehn, J.-M. Supramolecular Chemistry (VCH, Weinheim, 1995).

    Book  Google Scholar 

  4. Vögtle, F. Supramolecular Chemistry (Wiley, New York, 1991).

    Google Scholar 

  5. Philp, D. & Stoddart, J. F. Angew. Chem. Int. Edn Engl. 35, 1155–1196 (1996).

    CAS  Google Scholar 

  6. Eliel, E. L., Wilen, S. H. & Mander, L. N. Stereochemistry of Organic Compounds 864 (Wiley, New York, 1994).

    Google Scholar 

  7. Lutz, G. P., Du, H., Gallagher, D. J. & Beak, P. J. Org. Chem. 61, 4542–4554 (1996).

    Article  CAS  Google Scholar 

  8. Seebach, D. & Estermann, J. Tetrahedr. Lett. 28, 3103–3106 (1987).

    Article  CAS  Google Scholar 

  9. Seebach, D. Angew. Chem. Int. Edn Engl. 27, 1624–1654 (1988).

    Article  Google Scholar 

  10. Truce, W. E. & Klinger, T. C. J. Org. Chem. 35, 1834–1838 (1970).

    Article  CAS  Google Scholar 

  11. Thompson, C. M. Tetrahedr. Lett. 28, 4243–4246 (1987).

    Article  CAS  Google Scholar 

  12. Reich, H. J. & Gudmundsson, B. Ö. J. Am. Chem. Soc. 118, 6074–6075 (1996).

    Article  CAS  Google Scholar 

  13. Seebach, D., Bossler, H., Gründler, H., Shoda, S. & Wenger, R. Helv. Chim. Acta 74, 197–224 (1991).

    Article  CAS  Google Scholar 

  14. Illuminati, G. & Mandolini, L. Acc. Chem. Res. 14, 95–102 (1981).

    Article  CAS  Google Scholar 

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Author information

Authors and Affiliations

  1. Department of Chemistry and Biochemistry, University of Texas at Austin, Austin, Texas, 78712, USA

    Patrick Linnane, Nicholas Magnus & Philip Magnus

Authors
  1. Patrick Linnane
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  2. Nicholas Magnus
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  3. Philip Magnus
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Cite this article

Linnane, P., Magnus, N. & Magnus, P. Induction of molecular asymmetry by a remote chiral group. Nature 385, 799–801 (1997). https://doi.org/10.1038/385799a0

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  • Received: 05 November 1996

  • Accepted: 21 January 1997

  • Issue date: 27 February 1997

  • DOI: https://doi.org/10.1038/385799a0

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