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Synthesis of Aliphatic (E)-α,β-Unsaturated Amides with High Diastereoselectivity from α,β-Epoxyamides Promoted by SmI2/HMPA

✍ Scribed by José M. Concellón; Eva Bardales


Publisher
John Wiley and Sons
Year
2004
Tongue
English
Weight
104 KB
Volume
2004
Category
Article
ISSN
1434-193X

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Synthesis of (E)-α,β-Unsaturated Amides
✍ José M. Concellón; Juan A. Pérez-Andrés; Humberto Rodríguez-Solla 📂 Article 📅 2001 🏛 John Wiley and Sons 🌐 English ⚖ 129 KB 👁 1 views

Stereoselective b-elimination of 2-chloro-3-hydroxyamides 1 is achieved by using samarium diiodide to yield a,b-unsaturated amides 2, in which the C C bond is di-tri-, or tetrasubstituted. The starting compounds 1 are easily prepared by reaction of the corresponding lithium enolates of a-chloroamide