title: Foldamer-mediated remote stereocontrol: >1,60 asymmetric induction.
abstract: 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 Ac6 c. 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.
authors.affiliation: School of Chemistry, University of Manchester, Oxford Rd., Manchester M13 9PL (UK).
authors.forename: Liam
authors.initials: L
authors.lastname: Byrne
authors.forename: Jordi
authors.initials: J
authors.lastname: Solà
authors.forename: Thomas
authors.initials: T
authors.lastname: Boddaert
authors.forename: Tommaso
authors.initials: T
authors.lastname: Marcelli
authors.forename: Ralph W
authors.initials: RW
authors.lastname: Adams
authors.forename: Gareth A
authors.initials: GA
authors.lastname: Morris
authors.forename: Jonathan
authors.initials: J
authors.lastname: Clayden
keywords: acyliminium ions; asymmetric induction; helical molecules; peptides; remote stereocontrol