Tetrahedron p. 3041 - 3060 (1999)
Update date:2022-08-03
Topics:
Alvarez-Ibarra, Carlos
Csaky, Aurelio G.
Martinez-Santos, Elena
Quiroga, Maria L.
Tejedor, Jose L.
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.
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