title: Stereoselectivity of nitrile oxide cycloadditions to chiral allylic fluorides: experiment and theory.
abstract: The cycloadditions of nitrile oxides with new and previously studied allylic fluorides were examined. The 1,3-dipolar cycloaddition reactions were also investigated theoretically with density functional theory (B3LYP) based transition-state modelling. The predictions provided reasonable agreement with experiment, indicating that both steric and electronic effects have important influences on the stereoselectivities of these reactions.
authors.affiliation: ENSCR, Laboratoire de Synthèses et Activations de Biomolécules CNRS UMR 6052, Avenue de Général Leclerc, 35 700 Rennes Beaulieu, France.
authors.forename: Michael
authors.initials: M
authors.lastname: Prakesch
authors.forename: Danielle
authors.initials: D
authors.lastname: Grée
authors.forename: René
authors.initials: R
authors.lastname: Grée
authors.forename: Jennifer
authors.initials: J
authors.lastname: Carter
authors.forename: Ilyas
authors.initials: I
authors.lastname: Washington
authors.forename: K N
authors.initials: KN
authors.lastname: Houk
mesh_terms: D005459:Fluorides / Q000737:chemistry*; D006571:Heterocyclic Compounds / Q000737:chemistry; D008956:Models, Chemical; D009570:Nitriles / Q000737:chemistry*; D010087:Oxides / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D006571:Heterocyclic Compounds; D009570:Nitriles; D010087:Oxides; D005459:Fluorides