Mild Iridium-Catalysed Isomerization of Epoxides. Computational Insights and Application to the Synthesis of β-Alkyl Amines

Albert Cabré, Juanjo Cabezas-Giménez, Giuseppe Sciortino, Gregori Ujaque, Xavier Verdaguer, Agustí Lledós, Antoni Riera

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2 Citations (Scopus)

Abstract

© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim The isomerization of epoxides to aldehydes using the readily available Crabtree's reagent is described. The aldehydes were transformed into synthetically useful amines by a one-pot reductive amination using pyrrolidine as imine-formation catalyst. The reactions worked with low catalyst loadings in very mild conditions. The procedure is operationally simple and tolerates a wide range of functional groups. A DFT study of its mechanism is presented showing that the isomerization takes place via an iridium hydride mechanism with a low energy barrier, in agreement with the mild reaction conditions. (Figure presented.).
Original languageEnglish
Pages (from-to)3624-3631
JournalAdvanced Synthesis and Catalysis
Volume361
DOIs
Publication statusPublished - 1 Jan 2019

Keywords

  • Crabtree's catalyst
  • epoxides
  • iridium
  • isomerization
  • β-alkyl amines

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