Transmission of stereochemical information over nanometre distances in chemical reactions

Jonathan Clayden*

*Corresponding author for this work

Research output: Contribution to journalArticle (Academic Journal)

85 Citations (Scopus)


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.

Original languageEnglish
Pages (from-to)817-829
Number of pages13
JournalChemical Society Reviews
Issue number3
Early online date8 Dec 2008
Publication statusPublished - 1 Mar 2009

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