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Enantioselective two-phase hydrogenation of α-amino acid precursors with water soluble rhodium complexes of the cationic ligand (S,S)-2,4-bis[bis-(p-N,N,N-trimethylammoniumphenyl)phosphino]pentane, [CH3CH(P(p-C6H4NMe3)2CH2CH(P(p-C6H4NMe3)2CH3]4+

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Abstract

Rhodium complexes of the chiral cationic phosphine, (S,S)-2,4-bis[bis-(p-N,N.N-trimethyl-ammoniumphenyl)phosphino]pentane show excellent enantioselectivity for the hydrogenation of the DOPA precursor. (Z)-3-OMe,4-OAcC6H3CHC(COOH)(NHCOCH3), and dehydro-phenylalanineacetamide as slurries in water. The catalytic reactions may be done in either a two-phase system with the catalyst in the aqueous phase or as a slurry in water provided the substrates have some water solubility. Enantioselectivities of as high as 95% can be obtained.

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Authors and Affiliations

  1. Department of Chemistry, Virginia Polytechnic Institute and State University, 24061, Blacksburg, Virginia, USA

    Imre Tóth, Brian E. Hanson & Mark E. Davis

  2. Department of Chemical Engineering, Virginia Polytechnic Institute and State University, 24061, Blacksburg, Virginia, USA

    Mark E. Davis

Authors
  1. Imre Tóth
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  2. Brian E. Hanson
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  3. Mark E. Davis
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Tóth, I., Hanson, B.E. & Davis, M.E. Enantioselective two-phase hydrogenation of α-amino acid precursors with water soluble rhodium complexes of the cationic ligand (S,S)-2,4-bis[bis-(p-N,N,N-trimethylammoniumphenyl)phosphino]pentane, [CH3CH(P(p-C6H4NMe3)2CH2CH(P(p-C6H4NMe3)2CH3]4+ . Catal Lett 5, 183–188 (1990). https://doi.org/10.1007/BF00763951

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  • DOI: https://doi.org/10.1007/BF00763951

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