The benzyne aza-claisen reaction

Research output: Contribution to journalArticle

  • Authors:
  • Alastair A. Cant
  • Guillaume H V Bertrand
  • Jaclyn L. Henderson
  • Lee Roberts
  • Michael F. Greaney

Abstract

Adding an aryne to a tertiary allylamine affords oallylaniline products of an aza-Claisen rearrangement. The aryne simultaneously provides the π 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). © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.

Bibliographical metadata

Original languageEnglish
Pages (from-to)5199-5202
Number of pages3
JournalAngewandte Chemie - International Edition
Volume48
Issue number28
DOIs
StatePublished - 29 Jun 2009