title: Access to Constrained Fluoropseudopeptides via Ring-Closing Metathesis of Fluoroalkenes.
abstract: Bis-alkene substrates, containing one fluoroalkene and linked by an amide moiety, have been designed and synthesized to be subjected to ring-closing metathesis reactions. The substitution of fluoroalkene by a phenyl group enhanced the reactivity, and the resulting fluorinated lactams were obtained in high yields except when a hindered alkyl group was present in the molecule. The cycles were then subjected to ring opening in order to develop a new route to constrained fluoropseudopeptides bearing a fluoroalkene as a peptide bond mimic.
authors.affiliation: Normandie Université , ENSICAEN, Unicaen, CNRS, LCMT, 14000 Caen, France.
authors.forename: David
authors.initials: D
authors.lastname: Guérin
authors.affiliation: Normandie Université , ENSICAEN, Unicaen, CNRS, LCMT, 14000 Caen, France.
authors.forename: Isabelle
authors.initials: I
authors.lastname: Dez
authors.affiliation: Normandie Université , ENSICAEN, Unicaen, CNRS, LCMT, 14000 Caen, France.
authors.forename: Annie-Claude
authors.initials: AC
authors.lastname: Gaumont
authors.affiliation: Normandie Université , INSA Rouen, UNIROUEN, CNRS, COBRA, 76000 Rouen, France.
authors.forename: Xavier
authors.initials: X
authors.lastname: Pannecoucke
authors.affiliation: Normandie Université , INSA Rouen, UNIROUEN, CNRS, COBRA, 76000 Rouen, France.
authors.forename: Samuel
authors.initials: S
authors.lastname: Couve-Bonnaire
mesh_terms: D004151:Dipeptides / Q000138:chemical synthesis* / Q000737:chemistry; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry*; D008968:Molecular Conformation
chemical_list: D004151:Dipeptides; D006845:Hydrocarbons, Fluorinated