One-step synthesis of chiral dimethyl 2-oxo-3-phenyl-glutarate in the asymmetric triple-carbonylation of styrene

Article abstract of DOI:10.1016/S1872-2067(10)60253-7

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 = +27^o (c, 0.28, CH ₂Cl₂) for dimethyl 2-oxo-3-phenyl-glutarate using benzoquinone as oxidant, p-toluenesulfonic acid as co-catalyst, and methanol as solvent.