title: Asymmetric nucleophilic monofluorobenzylation of allyl and propargyl halides mediated by a remote sulfinyl group: synthesis of homoallylic and homopropargylic fluorides.
abstract: Fluorinated 2-(p-tolylsulfinyl)benzyl carbanions react with allyl and propargyl halides in a highly stereoselective way, providing homoallylic and homopropargylic fluorides, respectively, with high optical purity. Theoretical calculations found transition states for these transformations whose relative stabilities are consistent with the experimentally observed stereoselectivity.
authors: Departamento de Química Orgánica (EII), Universidad de Valladolid , Paseo del Cauce 59, 47011 Valladolid, Spain.
authors: Yolanda
authors: Y
authors: Arroyo
authors: M Ascensión
authors: MA
authors: Sanz-Tejedor
authors: Alejandro
authors: A
authors: Parra
authors: Inés
authors: I
authors: Alonso
authors: José Luis
authors: JL
authors: García Ruano
mesh_terms: D000838:Anions / Q000737:chemistry*; D001593:Benzyl Compounds / Q000737:chemistry*; D005459:Fluorides / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D010293:Pargyline / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry*; D011789:Quantum Theory; D013237:Stereoisomerism
chemical_list: D000838:Anions; D001593:Benzyl Compounds; D006845:Hydrocarbons, Fluorinated; D010293:Pargyline; D005459:Fluorides