title: Stereocontrolled fluorobenzylation of vinyl sulfones and α,β-unsaturated esters mediated by a remote sulfinyl group. Synthesis of functionalized enantiomerically pure benzylic fluorides.
abstract: A sulfinyl group in an ortho position confers enough chemical and configurational stability to monofluorobenzylcarbanions to evolve in a completely stereoselective way in their reactions with β-substituted vinyl sulfones and α,β-unsaturated esters. Reactions afford easily separable mixtures of two epimers differing in the configuration of the center derived from the Michael acceptor (up to 98% de). They can be easily converted into enantiomerically pure γ-fluorinated γ-phenylsulfones and γ-phenylesters bearing two chiral centers.
authors.affiliation: Departamento de Química Orgánica, Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain. joseluis.garcia.ruano@uam.es
authors.forename: José Luis
authors.initials: JL
authors.lastname: García Ruano
authors.forename: José Antonio
authors.initials: JA
authors.lastname: Fernández-Salas
authors.forename: M Carmen
authors.initials: MC
authors.lastname: Maestro
mesh_terms: D004952:Esters; D005459:Fluorides / Q000737:chemistry*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry*
chemical_list: D004952:Esters; D006845:Hydrocarbons, Fluorinated; D013450:Sulfones; C009873:divinyl sulfone; D005459:Fluorides