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

Research output: Contribution to journal › Article › peer-review

9 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 language	English
Pages (from-to)	5458-5460
Number of pages	3
Journal	Tetrahedron Letters
Volume	49
Issue number	38
DOIs	https://doi.org/10.1016/j.tetlet.2008.07.017
Publication status	Published - 2008 Sept 15

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2008.07.017

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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.",

author = "Nobutaka Ototake and Takeo Taguchi and Osamu Kitagawa",

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AU - Ototake, Nobutaka

AU - Taguchi, Takeo

AU - Kitagawa, Osamu

PY - 2008/9/15

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

JF - Tetrahedron Letters

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ER -

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

Abstract

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