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Synthesis of (E)-α,β-Unsaturated Amides with High Selectivity by Using Samarium Diiodide

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

Publisher: John Wiley and Sons
Year: 2001
Tongue: English
Weight: 129 KB
Volume: 7
Category: Article
ISSN: 0947-6539
DOI: 10.1002/1521-3765(20010716)7:14<3062::aid-chem3062>3.0.co;2-f

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✦ Synopsis

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-chloroamides with aldehydes or ketones at À 78 8C. The influence of the reaction conditions and the structure of the starting compounds on the stereoselectivity of the b-elimination reaction is also discussed.

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

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