73015-04-0Relevant academic research and scientific papers
Diastereoselective synthesis of syn,syn- and syn,anti-2,4-diamino-3- hydroxyglutaric acid derivatives from ethyl α-acyl alaninates
Alvarez-Ibarra, Carlos,Csaky, Aurelio G.,Martinez-Santos, Elena,Quiroga, Maria L.,Tejedor, Jose L.
, p. 3041 - 3060 (1999)
Syn,syn- and syn,anti-isomers of the four possible diastereomers of O,N,N'-protected 2,4-diamino-3-hydroxyglutaric acid derivatives 3-7 were diastereoselectively obtained. Syn,syn isomers of oxazolines 3 were selectively achieved by an aldol-like reaction in protic conditions between α-metallated ethyl isocyanoacetate 1 and α-acyl alaninates 2. Derivatives 4 with a syn,anti-configuration were obtained under epimerization reaction conditions, whereas derivatives 5-7 with a syn,syn-configuration were selectively obtained under kinetic reaction conditions.
