Application of Walphos Ligand in the Pd(0)-Catalyzed Asymmetric Allylic Alkylation Reaction

One relatively unexploited commercial ligand, Walphos 1, was tested in the Pd(0)-catalyzed asymmetric allylic alkylation using rac-1,3-diphenyl propenyl acetate and rac-1-acetoxycyclohexene as substrates, methyl malonate as nucleophile, and a variety of Pd precatalysts under standard conditions. The conversions and enantioselectivities were generally good, with the greatest substrate conversion of 99% and a greatest ee of 70%. With the latter cyclic substrate, an enantioselectivity of 98% was obtained, but the conversions were all poor (15-33%).