Collect. Czech. Chem. Commun. 2000, 65, 1580-1586

Convenient and Stereospecific Synthesis of trans-1,3-Disubstituted Imidazolidines and Their Transformation to 2,3-Diamino-3-phenylpropanoic Acids

Ivanka K. Kavrakova and Maria J. Lyapova*

Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Sciences, 1113 Sofia, Bulgaria


Conversion of the easily available trans-2-oxoimidazolidine-4-carboxylic acid 1 to the corresponding imidazolidines 8 gives after one-step oxidation and ring cleavage the diamino acid 2 in high yield. The difference in the trans-vicinal couplings for the hydrogen-bonded and nonbonded compounds suggests different ring geometry as a result of the balancing effect of the N1 substituent on the "allylic strain".

Keywords: Amino acids; 2,3-Diaminocarboxylic acids; Imidazolidines; Ring cleavage; Reductions; Steric interactions.

References: 11 live references.