Chiral Sulfonated Phosphines. 9. Role of Water in the Hydrogenation of Dehydro Amino Acids

József Bakos, Rita Karaivanov, Mohamed Laghmari, Denis Sinou

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Abstract

Homogeneous reduction of (Z)-α-acetamido- and (Z)-α-benzamidodocinnamic acid methyl ester and α-acetamidoacrylic acid methyl ester in an organic—water medium in the presence of a soluble catalyst obtained by mixing [Rh(COD)Cl]2 and a phosphine occurred with regiospecific incorporation of a deuterium atom at the position α to the acetamido and the ester group. When the reduction was performed under a deuterium atmosphere in the presence of water, hydrogen incorporation occurred at the same position and the overall reaction was a cis addition of HD. The amount of incorporation of deuterium depends on the nature of the phosphine, the solvent, and the amount of water. A mechanism involving a hydrogen—deuterium exchange on a α-rhodium monohydride intermediate is proposed.

Original languageEnglish
Pages (from-to)2951-2956
Number of pages6
JournalOrganometallics
Volume13
Issue number8
DOIs
Publication statusPublished - Aug 1 1994

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ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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