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

Nobutaka Ototake; Takeo Taguchi; Osamu Kitagawa

doi:10.1016/j.tetlet.2008.07.017

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

Nobutaka Ototake, Takeo Taguchi, Osamu Kitagawa

研究成果: Article › 査読

9 被引用数 (Scopus)

抄録

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.

本文言語	English
ページ（範囲）	5458-5460
ページ数	3
ジャーナル	Tetrahedron Letters
巻	49
号	38
DOI	https://doi.org/10.1016/j.tetlet.2008.07.017
出版ステータス	Published - 2008 9月 15

ASJC Scopus subject areas

生化学
創薬
有機化学

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10.1016/j.tetlet.2008.07.017

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AU - Taguchi, Takeo

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Y1 - 2008/9/15

N2 - 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.

AB - 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.

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JO - Tetrahedron Letters

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

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