This work was funded by the European Research Council through Advanced Grant ROCOCO and by the EPSRC through grant EP/I007989. We thank Dr. James Raftery for determining the X-ray crystal structure of 6 b.
Foldamer-Mediated Remote Stereocontrol: >1,60 Asymmetric Induction†
Article first published online: 8 NOV 2013
Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Volume 126, Issue 1, pages 155–159, January 3, 2014
How to Cite
Byrne, L., Solà, J., Boddaert, T., Marcelli, T., Adams, R. W., Morris, G. A. and Clayden, J. (2014), Foldamer-Mediated Remote Stereocontrol: >1,60 Asymmetric Induction. Angew. Chem., 126: 155–159. doi: 10.1002/ange.201308264
- Issue published online: 23 DEC 2013
- Article first published online: 8 NOV 2013
- Manuscript Received: 20 SEP 2013
- European Research Council
- EPSRC. Grant Number: EP/I007989
- Asymmetrische Induktion;
- Helicale Moleküle;
An N-terminal L-α-methylvaline dimer induces complete conformational control over the screw sense of an otherwise achiral helical peptide foldamer formed from the achiral quaternary amino acids Aib and Ac6c. The persistent right-handed screw-sense preference of the helix enables remote reactive sites to fall under the influence of the terminal chiral residues, and permits diastereoselective reactions such as alkene hydrogenation or iminium ion addition to take place with 1,16-, 1,31-, 1,46- and even 1,61-asymmetric induction. Stereochemical information may be communicated in this way over distances of up to 4 nm.