Stereoselective synthesis of separable amide rotamers using π-allyl-Pd catalyst and their thermodynamic behavior

Nobutaka Ototake, Takeo Taguchi, Osamu Kitagawa

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8 Citations (Scopus)


Separable amide rotamers were prepared with moderate to excellent Z-selectivities by N-allylation of 2,4,6-tri-tert-butyl-NH-anilides using a π-allyl-Pd catalyst. The present allylation proceeded through a unique mechanism involving O-allylation and the subsequent O,N-allylic rearrangement. The prepared amide rotamers of Z-major changed to equilibrium mixtures of E-major when heated in toluene.

Original languageEnglish
Pages (from-to)5458-5460
Number of pages3
JournalTetrahedron Letters
Issue number38
Publication statusPublished - 2008 Sep 15


ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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