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ChemInform Abstract: Synthesis of Isotopically Labeled (E)-β,γ-Unsaturated Esters with Total or High E/Z—Selectivity by Using Samarium Diiodide.

✍ Scribed by Jose M. Concellon; Pablo L. Bernad; Humberto Rodriguez-Solla

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

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Synthesis of Isotopically Labeled (E)-β,
Synthesis of Isotopically Labeled (E)-β,γ-Unsaturated Esters with Total or High Diastereoselectivity by Using Samarium Diiodide
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A simple, efficient, highly diastereoselective method for preparing (E)-α,δ-dideuterio-β,γ-unsaturated esters: SmI -promoted reduction/elimination of α-halo-β-hydroxy-γ,δ-unsaturated esters in the presence of D O. This provides the desired products in which the C-C double bond is generated with tota

Synthesis of (E)-α,β-Unsaturated Amides
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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