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Mild Iridium‐Catalysed Isomerization of Epoxides. Computational Insights and Application to the Synthesis of β‐Alkyl Amines
Author(s) -
Cabré Albert,
CabezasGiménez Juanjo,
Sciortino Giuseppe,
Ujaque Gregori,
Verdaguer Xavier,
Lledós Agustí,
Riera Antoni
Publication year - 2019
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201900372
Subject(s) - chemistry , isomerization , iridium , catalysis , imine , alkyl , reductive amination , reagent , pyrrolidine , hydride , amination , combinatorial chemistry , organic chemistry , photochemistry , metal
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.