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Synlett 1991; 1991(1): 49-51
DOI: 10.1055/s-1991-20625
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Development of a New Six-Membered Chelating Chiral [Bisphosphine] rhodium Catalyst and Efficient Asymmetric Hydrogenation of (Z)-2-Acetamidocinnamic Acid1

Kiyoshi Inoguchi* , Kazuo Achiwa
  • *School of Pharmaceutical Sciences, University of Shizuoka, 395 Yada, Shizuoka 422, Japan
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Publikationsdatum:
07. März 2002 (online)

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A new 1,3-substituted bisphosphine ligand, (1R, 2R)-1- diphenylphosphino - 2- (diphenylphosphinomethyl) - cyclopentane (R,R)-PPCP, was prepared in four steps from ethyl 2-oxocyclopentanecarboxylate. (R,R)-PPCP was designed to form the favorable skew conformation of the six-membered chelate with rhodium. Its rhodium complex was found to be one of the most efficient catalysts for asymmetric catalytic hydrogenation of amino acid precursors such as (Z)-2-acetamidocinnamic acid.