125281-47-2Relevant academic research and scientific papers
Approach to Chiral Vicinal Diacylamines by Bamberger Ring Cleavage of Substituted Imidazoles
Altman, Janina,Grinberg, Mircea,Wilchek, Meir
, p. 339 - 343 (2007/10/02)
Ring cleavage of ethyl 3-propanoate (1) with (-)-menthyl chloroformate introduces chiral carbamate substituents on the double bond which, upon hydrogenation, induces preferred formation of ethyl (4S)-4,5-bispentanoate (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.
