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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 Jose M. Concellon; Eva Bardales

Publisher: John Wiley and Sons
Year: 2004
Weight: 121 KB
Volume: 35
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.200431072

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✦ Synopsis

Abstract

For Abstract see ChemInform Abstract in Full Text.

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## Abstract For Abstract see ChemInform Abstract in Full Text.

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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

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