title: Palladium-Catalyzed Alkene Carboamination Reactions of Electron-Poor Nitrogen Nucleophiles.
abstract: Modified reaction conditions that facilitate Pd-catalyzed alkene carboamination reactions of electron-deficient nitrogen nucleophiles are reported. Pent-4-enylamine derivatives bearingN-tosyl orN-trifluoroacetyl groups are coupled with aryl triflates to afford substituted pyrrolidines in good yield. These reactions proceed via a mechanism involvinganti-aminopalladation of the alkene, which differs from previously reported analogous reactions ofN-aryl andN-boc pentenylamines. The application of these conditions to a formal synthesis of (±)-aphanorphine is also described.
authors.affiliation: University of Michigan, Department of Chemistry, 930 N. University Ave., Ann Arbor, MI, 48109-1055, USA. Ph: +1 (734)-763-3432.
authors.forename: Luke J
authors.initials: LJ
authors.lastname: Peterson
authors.affiliation: University of Michigan, Department of Chemistry, 930 N. University Ave., Ann Arbor, MI, 48109-1055, USA. Ph: +1 (734)-763-3432.
authors.forename: John P
authors.initials: JP
authors.lastname: Wolfe
keywords: Alkenes; Aryl Halides; Heterocycles; Palladium