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Z-Selective Synthesis of α,β-Unsaturated Amides with Triphenylsilylacetamides.

✍ Scribed by Satoshi Kojima; Hiroki Inai; Tsugihiko Hidaka; Tomohide Fukuzaki; Katsuo Ohkata


Publisher
John Wiley and Sons
Year
2010
Weight
34 KB
Volume
33
Category
Article
ISSN
0931-7597

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✦ Synopsis


Abstract

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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