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

✍ Scribed by Nobutaka Ototake; Takeo Taguchi; Osamu Kitagawa

Book ID: 104095589
Publisher: Elsevier Science
Year: 2008
Tongue: French
Weight: 200 KB
Volume: 49
Category: Article
ISSN: 0040-4039
DOI: 10.1016/j.tetlet.2008.07.017

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✦ Synopsis

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 p-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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