Chiral sulfonated phosphines. 9. Role of water in the hydrogenation of dehydro amino acids

J. Bakos, Rita Karaivanov, Mohamed Laghmari, Denis Sinou

Research output: Contribution to journalArticle

37 Citations (Scopus)

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 σ-rhodium monohydride intermediate is proposed.

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

Fingerprint

Phosphines
phosphine
Deuterium
phosphines
Hydrogenation
hydrogenation
amino acids
deuterium
Amino Acids
esters
Esters
Water
water
Hydrogen
Rhodium
acids
Acids
crack opening displacement
hydrogen
rhodium

ASJC Scopus subject areas

  • Inorganic Chemistry
  • Organic Chemistry

Cite this

Chiral sulfonated phosphines. 9. Role of water in the hydrogenation of dehydro amino acids. / Bakos, J.; Karaivanov, Rita; Laghmari, Mohamed; Sinou, Denis.

In: Organometallics, Vol. 13, No. 8, 1994, p. 2951-2956.

Research output: Contribution to journalArticle

Bakos, J, Karaivanov, R, Laghmari, M & Sinou, D 1994, 'Chiral sulfonated phosphines. 9. Role of water in the hydrogenation of dehydro amino acids', Organometallics, vol. 13, no. 8, pp. 2951-2956.
Bakos, J. ; Karaivanov, Rita ; Laghmari, Mohamed ; Sinou, Denis. / Chiral sulfonated phosphines. 9. Role of water in the hydrogenation of dehydro amino acids. In: Organometallics. 1994 ; Vol. 13, No. 8. pp. 2951-2956.
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