Convenient and Stereospecific Synthesis of trans-1,3-Disubstituted Imidazolidines and Their Transformation to 2,3-Diamino-3-phenylpropanoic Acids
2000 ◽
Vol 65
(10)
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pp. 1580-1586
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Keyword(s):
One Step
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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".