title: Stereoselective synthesis of both stereoisomers of β-fluorostyrene derivatives from a common intermediate.
abstract: The stereoselective synthesis of both cis- and trans-β-fluorostyrene derivatives from a common intermediate, (Z)-1-aryl-2-fluoro-1-(trimethylsilyl)ethenes, is described. The trans isomers are obtained by a stereospecific replacement of the silyl group in the presence of water and a fluoride source, whereas the preparation of the cis isomers is achieved by a bromination/desilicobromination sequence followed by reduction of the newly created C-Br bond. A stereoselective transformation of both stereoisomers of β-fluorostyrene is also presented.
authors.affiliation: Département de chimie, 1045 avenue de la Médecine, Université Laval, Québec, QC, Canada G1V 0A6.
authors.forename: Grégory
authors.initials: G
authors.lastname: Landelle
authors.forename: Marc-Olivier
authors.initials: MO
authors.lastname: Turcotte-Savard
authors.forename: Laetitia
authors.initials: L
authors.lastname: Angers
authors.forename: Jean-François
authors.initials: JF
authors.lastname: Paquin
mesh_terms: D002384:Catalysis; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013343:Styrenes / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D006845:Hydrocarbons, Fluorinated; D013343:Styrenes