Article citationsMore>>

Harada, K. and Kataoka, Y. (1978) Asymmetric Synthesis of Alanine by Hydrogenolytic Asymmetric Transamination. Tetrahedron Letters, 19, 2103-2106.
http://dx.doi.org/10.1016/S0040-4039(01)94761-6

has been cited by the following article:

• TITLE: Diastereoselective Catalytic Hydrogenation of Schiff Bases of N-Pyruvoyl-(S)-Proline Esters

  AUTHORS: Toratane Munegumi, Shokichi Ohuchi, Kaoru Harada

  KEYWORDS: Diastereoselective; Catalytic Hydrogenation; Proline; Pyruvamide; Schiff Base

  JOURNAL NAME: International Journal of Organic Chemistry, Vol.4 No.1, March 4, 2014

  ABSTRACT: Diastereoselective catalytic hydrogenation of pyruvic acid esters, amides, and their Schiff bases has been well studied over a long period to show that proline is one of the most effective chiral auxiliaries. Proline derivatives have been used as auxiliaries in the diastereoselective catalytic hydrogenation of pyruvamide Schiff bases. The diastereoselective hydrogenation resulted in up to a 78% enantiomeric excess of the amino acid derived from the hydrolysis of the dipeptide products. The chelation hypothesis explains the stereochemistry of the catalytic hydrogenation using (S)-proline esters in the amide moiety and the two chiral centers in the amide and Schiff base moieties.