title: Absolute control of helical handedness in quinoline oligoamides.
abstract: The synthesis of quinoline-derived helically folded aromatic oligoamides functionalized by various chiral functions at their N-terminus is reported. When a (1S)-(-)-camphanyl moiety was introduced, it was found that helix handedness was completely shifted to right-handed helicity (de > 99%), in both protic and nonprotic solvents. The absolute helical sense and the de values were unambiguously characterized by using (1)H NMR, circular dichroism (CD), and X-ray crystallography. The crystal structure of these compounds allowed us to propose a rationale for the efficiency of helix handedness induction based on a combination of steric factors and intramolecular hydrogen bonding.
authors.affiliation: Institut Européen de Chimie et Biologie, Université de Bordeaux-CNRS UMR 5248 and UMS 3033, 2 rue Robert Escarpit, F-33607 Pessac, France.
authors.forename: Amol M
authors.initials: AM
authors.lastname: Kendhale
authors.forename: Legiso
authors.initials: L
authors.lastname: Poniman
authors.forename: Zeyuan
authors.initials: Z
authors.lastname: Dong
authors.forename: Katta
authors.initials: K
authors.lastname: Laxmi-Reddy
authors.forename: Brice
authors.initials: B
authors.lastname: Kauffmann
authors.forename: Yann
authors.initials: Y
authors.lastname: Ferrand
authors.forename: Ivan
authors.initials: I
authors.lastname: Huc