title: Chemoselective, Substrate-directed Fluorination of Functionalized Cyclopentane β-Amino Acids.
abstract: This work describes a substrate-directed fluorination of some highly functionalized cyclopentane derivatives. The cyclic products incorporating CH2F or CHF2moieties in their structure have been synthesized from diexo- or diendo-norbornene β-amino acids following a stereocontrolled strategy. The synthetic study was based on an oxidative transformation of the ring carbon-carbon double bond of the norbornene β-amino acids, followed by transformation of the resulted "all cis" and "trans" diformyl intermediates by fluorination with "chemodifferentiation".
authors: Institute of Pharmaceutical Chemistry, University of Szeged, 6720, Szeged, Eötvös u. 6, Hungary.
authors: Loránd
authors: L
authors: Kiss
authors: MTA-SZTE Stereochemistry Research Group, Hungarian Academy of Sciences, 6720, Szeged, Eötvös u. 6, Hungary.
authors: Melinda
authors: M
authors: Nonn
authors: Department of Chemistry, University of Jyväskylä, 40014, Jyväskylä, Finland.
authors: Reijo
authors: R
authors: Sillanpää
authors: Department of Chemistry, University of Jyväskylä, 40014, Jyväskylä, Finland.
authors: Matti
authors: M
authors: Haukka
authors: Universidad de Valencia, Facultad de Farmàcia, Departamento de Química Orgánica, Av. Vicente Andrés Estellés, s/n, 46100, Valencia, Spain.
authors: Santos
authors: S
authors: Fustero
authors: Institute of Pharmaceutical Chemistry, University of Szeged, 6720, Szeged, Eötvös u. 6, Hungary.|MTA-SZTE Stereochemistry Research Group, Hungarian Academy of Sciences, 6720, Szeged, Eötvös u. 6, Hungary.
authors: Ferenc
authors: F
authors: Fülöp
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003500:Cyclization; D003517:Cyclopentanes / Q000737:chemistry*; D054879:Halogenation; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry; D008968:Molecular Conformation; D010084:Oxidation-Reduction; D013237:Stereoisomerism
chemical_list: D000596:Amino Acids; D003517:Cyclopentanes; D006845:Hydrocarbons, Fluorinated; C029999:fluoromethane
keywords: amino acids; cyclization; fluorine; molecular diversity; substituent effects