Synthesis and Application of Chiral P,N-Ligands with Pseudo-Meso and Pseudo-C 2 Symmetry

Two diastereoisomeric P,N-ligands, (S,S)-1 and (R,S)-1, were synthesized and assessed in palladium-catalyzed allylic alkylations. With rac-1,3-diphenylpropenyl acetate as substrate, ligand (S,S)-1, with “pseudo-C 2” symmetry, exhibited higher reactivity and higher enantioselectivity than the “pseudo-meso” ligand (R,S)-1, whereas reversal reactivity and selectivity were observed with rac-3-cyclohexenyl acetate.