Highly Selective Stereodivergent Synthesis of Separable Amide Rotamers, by Using Pd Chemistry, and Their Thermodynamic Behavior

Stereoselective synthesis of separable a

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

✍ Nobutaka Ototake; Takeo Taguchi; Osamu Kitagawa 📂 Article 📅 2008 🏛 Elsevier Science 🌐 French ⚖ 200 KB

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 prep