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Keywords:

  • amides;
  • Claisen rearrangement;
  • iminiums;
  • keteniminium;
  • rearrangement
Thumbnail image of graphical abstract

Rearranging its feathers: The transformation of simple linear amides into a diverse range of branched, functionalized products by conversion to iminium esters is followed by sequential treatment with nucleophiles and electrophiles (see scheme). The method takes advantage of a novel Claisen rearrangement and the use of aromatic substrates greatly facilitates the formation of the intermediate iminium ether.