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Foldamer-Mediated Remote Stereocontrol: >1,60 Asymmetric Induction


  • 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.


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.