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Synthesis of (E)-alpha,beta-unsaturated amides with high selectivity by using samarium diiodide
J M Concellón1, J A Pérez-Andrés, H Rodríguez-Solla
1Departamento de Química Orgánica e Inorgánica, Facultad de Química, Universidad de Oviedo, Spain. jmcg@sauron.quimica.uniovi.es
Chemistry (Weinheim an Der Bergstrasse, Germany)
|August 10, 2001
Abstract:
Stereoselective beta-elimination of 2-chloro-3-hydroxyamides 1 is achieved by using samarium diiodide to yield alpha,beta-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 alpha-chloroamides with aldehydes or ketones at - 78 degrees C. The influence of the reaction conditions and the structure of the starting compounds on the stereoselectivity of the beta-elimination reaction is also discussed.