title: The benzyne aza-Claisen reaction.
abstract: Adding an aryne to a tertiary allylamine affords o-allylaniline products of an aza-Claisen rearrangement. The aryne simultaneously provides the pi component for the rearrangement and the quaternization event that lowers the activation energy for the sigmatropic shift. The reaction was applied to the synthesis of medium-ring benzannulated amines (see scheme).
authors.affiliation: School of Chemistry, University of Edinburgh, King's Buildings, West Mains Road, Edinburgh, EH9 3JJ, UK.
authors.forename: Alastair A
authors.initials: AA
authors.lastname: Cant
authors.forename: Guillaume H V
authors.initials: GH
authors.lastname: Bertrand
authors.forename: Jaclyn L
authors.initials: JL
authors.lastname: Henderson
authors.forename: Lee
authors.initials: L
authors.lastname: Roberts
authors.forename: Michael F
authors.initials: MF
authors.lastname: Greaney
mesh_terms: D000588:Amines / Q000737:chemistry; D001372:Aza Compounds / Q000737:chemistry*; D001555:Benzene Derivatives / Q000737:chemistry*; D002384:Catalysis; D010880:Piperidines / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D000588:Amines; D001372:Aza Compounds; D001555:Benzene Derivatives; D010880:Piperidines; C524146:benzyne