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 language | English |
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Pages (from-to) | 3624-3631 |
Journal | Advanced Synthesis and Catalysis |
Volume | 361 |
DOIs | |
Publication status | Published - 1 Jan 2019 |
Keywords
- Crabtree's catalyst
- epoxides
- iridium
- isomerization
- β-alkyl amines