J. Altman, M. Grinberg, M. Wilchek
Apr 12, 1990
Citations
0
Influential Citations
4
Citations
Journal
European Journal of Organic Chemistry
Abstract
Ring cleavage of ethyl 3-[4(5)-imidazolyl]propanoate (1) with (−)-menthyl chloroformate introduces chiral carbamate substituents on the double bond which, upon hydrogenation, induces preferred formation of ethyl (4S)-4,5-bis[(−)-menthyl-oxycarbonylamino]pentanoate (5) (5:1 ratio of diastereomers). The ring cleavage benzoylation product of (S)-histidine methyl ester, with a chiral center in the side chain, gives rise to (2S,4R)/(2S,4S)-2,4,5-tribenzamidopentanoates (13, 14), in 2:1 ratio upon hydrogenation.