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Issue 3, 2009
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Transmission of stereochemical information over nanometre distances in chemical reactions

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Abstract

By exploiting intramolecular interactions such as dipole repulsion, and by incorporating a terminal chiral controlling feature, the global conformation of a molecule may be governed. In such an environment, stereoselective reactions can occur at considerable distances from the source of stereochemical information, providing a simple method for information relay over scales of >1 nm (or about seven bond lengths). This tutorial review discusses the development of this idea, and describes examples which depend on relayed dipole repulsion and on the absolute control of helicity. Future prospects in the area employing control over extended helical foldamers are elaborated.

Graphical abstract: Transmission of stereochemical information over nanometre distances in chemical reactions

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Publication details

The article was received on 10 Oct 2008 and first published on 08 Dec 2008


Article type: Tutorial Review
DOI: 10.1039/B801639A
Citation: Chem. Soc. Rev., 2009,38, 817-829
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    Transmission of stereochemical information over nanometre distances in chemical reactions

    J. Clayden, Chem. Soc. Rev., 2009, 38, 817
    DOI: 10.1039/B801639A

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