One-Step Synthesis of Chiral Dimethyl 2-Oxo-3-phenyl-glutarate in the Asymmetric Triple-carbonylation of Styrene

The in situ preparation of the novel chiral catalyst system, which are composed of (S)-2,2′,6,6′-tetramethoxy- 4,4′-bis(diphenylphosphine)-3,3′-bipyridine ((S)-P-PHOS) and palladium 2,4-pentanedionate, have been described. These complexes were found to be effective in the asymmetric triple-carbonylation of styrene, reaching up to [α]D20 = +27o (c, 0.28, CH2Cl2) for dimethyl 2-oxo-3-phenyl-glutarate using benzoquinone as oxidant, p-toluenesulfonic acid as co-catalyst, and methanol as solvent.