title: Alkene substituents for selective activation of endo-regioselective polyepoxide oxacyclizations.
abstract: The presence of an alkenyl substituent on the terminal epoxide of a polyepoxide substrate enhances the yield of all-endo-regioselective tandem oxacyclization to trans-syn-trans-fused polycyclic ethers. For a substrate in which the epoxide and alkene functional groups are separated by two methylene substituents, a novel bromonium ion-induced endo-regioselective cyclization to bromooxepane is also described. [reaction: see text]
authors.affiliation: Department of Chemistry, Emory University, Atlanta, GA 30322, USA.
authors.forename: Fernando
authors.initials: F
authors.lastname: Bravo
authors.forename: Frank E
authors.initials: FE
authors.lastname: McDonald
authors.forename: Wade A
authors.initials: WA
authors.lastname: Neiwert
authors.forename: Kenneth I
authors.initials: KI
authors.lastname: Hardcastle
mesh_terms: D000475:Alkenes / Q000737:chemistry*; D003500:Cyclization; D004852:Epoxy Compounds / Q000737:chemistry*; D011083:Polycyclic Compounds / Q000138:chemical synthesis*
chemical_list: D000475:Alkenes; D004852:Epoxy Compounds; D011083:Polycyclic Compounds