title: A Stereocontrolled Protocol to Highly Functionalized Fluorinated Scaffolds through a Fluoride Opening of Oxiranes.
abstract: A novel selective and substrate-dependent synthetic protocol has been developed towards the synthesis of various fluorine-containing, highly functionalized cycloalkane derivatives. The method involves the stereoselective epoxidation of some unsaturated cyclic β-amino acid derivatives as model compounds, followed by a regioselective fluoride opening of oxiranes under various conditions with Deoxofluor and XtalFluor-E reagents, thereby offering an insight into this new epoxide opening methodology with fluoride.
authors.affiliation: Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, H-6720 Szeged, Hungary. remete.attila@pharm.u-szeged.hu.
authors.forename: Attila Márió
authors.initials: AM
authors.lastname: Remete
authors.affiliation: MTA-SZTE Stereochemistry Research Group, Hungarian Academy of Sciences, Eötvös u. 6, H-6720 Szeged, Hungary. nonn.melinda@pharm.u-szeged.hu.
authors.forename: Melinda
authors.initials: M
authors.lastname: Nonn
authors.affiliation: Departamento de Química Orgánica, Facultad de Farmacia, Universidad de Valencia, Av. Vicente Andrés Estellés, s/n 46100 Valencia, Spain. Santos.Fustero@uv.es.
authors.forename: Santos
authors.initials: S
authors.lastname: Fustero
authors.affiliation: Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, H-6720 Szeged, Hungary. fulop@pharm.u-szeged.hu.|MTA-SZTE Stereochemistry Research Group, Hungarian Academy of Sciences, Eötvös u. 6, H-6720 Szeged, Hungary. fulop@pharm.u-szeged.hu.
authors.forename: Ferenc
authors.initials: F
authors.lastname: Fülöp
authors.affiliation: Institute of Pharmaceutical Chemistry, University of Szeged, Eötvös u. 6, H-6720 Szeged, Hungary. kiss.lorand@pharm.u-szeged.hu.
authors.forename: Loránd
authors.initials: L
authors.lastname: Kiss
mesh_terms: D000475:Alkenes; D004852:Epoxy Compounds / Q000737:chemistry*; D005459:Fluorides / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry; D013237:Stereoisomerism; D013457:Sulfur Compounds / Q000737:chemistry
chemical_list: D000475:Alkenes; D004852:Epoxy Compounds; D006845:Hydrocarbons, Fluorinated; D013457:Sulfur Compounds; C551695:diethylaminodifluorosulfinium tetrafluoroborate; D005459:Fluorides
keywords: amino acids; fluorination; oxirane; regioselectivity; stereoselectivity