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.
ASJC Scopus subject areas
- Physical and Theoretical Chemistry
- Organic Chemistry
- Inorganic Chemistry