Diastereoselective synthesis of syn,syn- and syn,anti-2,4-diamino-3-hydroxyglutaric acid derivatives from ethyl α-acyl alaninates

Autor:	Aurelio G. Csaky, M. L. Quiroga, Carlos Alvarez-Ibarra, JoséL Tejedor, E. Martinez‐Santos
Rok vydání:	1999
Předmět:	Reaction conditions Chemistry Stereochemistry Organic Chemistry Drug Discovery Diastereomer Epimer Biochemistry
Zdroj:	Tetrahedron. 55:3041-3060
ISSN:	0040-4020
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::f5dfa8fa5fb8538b91d02466e5c9e5bb https://doi.org/10.1016/s0040-4020(99)00065-4 Zobrazit plný text záznamu Full Text from ScienceDirect