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

…, JA Pérez??Andrés, H Rodríguez??Solla

Index: Concellon, Jose M.; Perez-Andres, Juan A.; Rodriguez-Solla, Humberto Chemistry - A European Journal, 2001 , vol. 7, # 14 p. 3062 - 3068

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Citation Number: 35

Abstract

Abstract Stereoselective β-elimination of 2-chloro-3-hydroxyamides 1 is achieved by using samarium diiodide to yield α, β-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 α-chloroamides with aldehydes or ketones at− 78 C. The influence of the reaction conditions and the structure of the starting compounds on the ...