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

Nobutaka Ototake, Takeo Taguchi, Osamu Kitagawa

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

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
Volume49
Issue number38
DOIs
Publication statusPublished - 2008 Sep 15

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Allylation
Amides
Thermodynamics
Catalysts
Anilides
Toluene

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Stereoselective synthesis of separable amide rotamers using π-allyl-Pd catalyst and their thermodynamic behavior. / Ototake, Nobutaka; Taguchi, Takeo; Kitagawa, Osamu.

In: Tetrahedron Letters, Vol. 49, No. 38, 15.09.2008, p. 5458-5460.

Research output: Contribution to journalArticle

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