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Keywords:

  • allylation;
  • amides;
  • cyanation;
  • cyclization;
  • macrocycles
Thumbnail image of graphical abstract

Take the direct path: Sequential nucleophilic addition of N-methoxyamides using DIBAL and organometallic reagents provided substituted N-methoxyamines in one pot via five-membered chelated intermediates (see scheme, DIBAL=diisobutylaluminum hydride). The reaction allows functionalization of acyclic amides and macrolactams without a preactivation step, which is generally required for inert amide carbonyl groups.