Iron‐<i>N</i>,<i>N</i>,<i>N’</i>,<i>N</i>’‐Tetramethylethylenediamine‐Catalyzed Selective Substitution of Functionalized Diene and Triene Monoepoxides with Aliphatic Grignard Reagents

Abstract When γ,δ‐epoxy‐α,β‐unsaturated esters were treated with 3 equiv. of aliphatic Grignard reagents in the presence of 10 and 20 mol% FeCl 2 and N , N , N ’, N ’‐tetramethylethylenediamine, regio‐ and stereoselective substitution of the epoxide moiety with the aliphatic Grignard reagent occurred, producing exclusively δ‐hydroxy‐γ‐alkyl‐α,β‐unsaturated esters. Similarly, γ,δ‐epoxy‐α,β,ϵ,ζ‐unsaturated esters and amides underwent transformation to the corresponding δ‐hydroxy‐γ‐alkyl‐α,β,ϵ,ζ‐unsaturated esters and amides as single isomers, respectively.