title: Enantiospecific bromonium ion generation and intramolecular capture: a model system for asymmetric bromonium ion-induced polyene cyclisations.
abstract: Scalemic bromonium ions generated enantiospecifically by the action of catalytic triflic acid on scalemic regioisomeric bromohydrin derivatives are trapped intramolecularly, enantiospecifically and regioselectively to give bicyclic brominated carbocycles in excellent yield and high enantiomeric excess. This enantiospecific pathway is not significantly perturbed by the addition of a trisubstituted alkene.
authors.affiliation: Department of Chemistry, Imperial College London, London, SW7 2AZ, UK. c.braddock@imperial.ac.uk
authors.forename: D Christopher
authors.initials: DC
authors.lastname: Braddock
authors.forename: Jared S
authors.initials: JS
authors.lastname: Marklew
authors.forename: Alexander J F
authors.initials: AJ
authors.lastname: Thomas
mesh_terms: D000438:Alcohols / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D054879:Halogenation; D006842:Hydrocarbons, Brominated / Q000138:chemical synthesis* / Q000737:chemistry; D007477:Ions / Q000737:chemistry; D011090:Polyenes / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D006842:Hydrocarbons, Brominated; D007477:Ions; D011090:Polyenes; C023963:bromohydrins