Palladium-catalyzed asymmetric allylic substitutions in the presence of chiral phosphine-imine type ligands

Chiral bidentate phosphine-imine type ligand L9 is fairly effective in the asymmetric allylic substitution of 1,3-diphenylpropenyl acetate with dimethyl malonate to give the corresponding adduct in moderate yield and good ee.

Chiral phosphine-imine type ligand L9 prepared from (R)-(−)-2-(diphenylphosphino)-1,1′-binaphthyl-2′-amine is fairly effective in the asymmetric allylic substitution of 1,3-diphenylpropenyl acetate with dimethyl malonate. Its bidentate coordination pattern to a Pd metal center with both P and N atoms has been unambiguously established by X-ray diffraction.Figure optionsDownload as PowerPoint slideHighlights
► Chiral bidentate phosphine-imine type ligands are fairly effective in the asymmetric allylic substitution.
► The corresponding adducts could be obtained in moderate yields and good ee values.
► The coordination pattern to the Pd metal center has been unambiguously established by X-ray diffraction.