Chinese Journal of Catalysis ›› 2011, Vol. 32 ›› Issue (7): 1143-1148.DOI: 10.1016/S1872-2067(10)60253-7

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

WANG Lailai*, ZHANG Qinsheng, CUI Yuming   

  1. State Key Laboratory for Oxo Synthesis & Selective Oxidation, Lanzhou Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou 730000, Gansu, China
  • Received:2011-03-25 Revised:2011-05-28 Online:2011-07-18 Published:2014-11-28

Abstract: The in-situ preparation of the novel chiral catalyst precursor, 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.

Key words: styrene, asymmetric triple-carbonylation, chiral, dimethyl 2-oxo-3-phenyl-glutarate, palladium 2,4-pentanedionate, dipyridlphosphines