Transmission of stereochemical information over nanometre distances in chemical reactions

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.