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 ...
