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Synthesis of (E)-α,β-Unsaturated Esters and Amides with Total Selectivity Using Samarium Diiodide

✍ Scribed by José M. Concellón; Juan A. Pérez-Andrés; Humberto Rodríguez-Solla


Publisher
John Wiley and Sons
Year
2000
Tongue
English
Weight
79 KB
Volume
39
Category
Article
ISSN
0044-8249

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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

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