Collect. Czech. Chem. Commun.
2000, 65, 1580-1586
https://doi.org/10.1135/cccc20001580
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
Abstract
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.
