Oxidation of didehydro-α-amino acids as a route to β-hydroxy-or β-amino-pyruvic derivatives and to α-acylglycinates

Autor:	Loïc Toupet, Daniel Danion, Renée Danion-Bougot, Helene Rudyk, Benoît Miossec
Rok vydání:	1996
Předmět:	chemistry.chemical_classification Hydrolysis Bromine Chemistry Intramolecular force Organic chemistry chemistry.chemical_element Medicinal chemistry Amino acid
Zdroj:	J. Chem. Soc., Perkin Trans. 1. :1833-1837
ISSN:	1364-5463 0300-922X
DOI:	10.1039/p19960001833
Popis:	Oxidation of protected didehydro-α-amino acids with N-bromosuccinimide or lead tetraacetate affords imines of β-bromo- or β-acetoxy-pyruvates. The hydrolysis of brominated imines proceeds through addition of water followed by intramolecular displacement of bromine. According to experimental procedures, intermediate hydroxyaziridines, hydroxyoxazolines or aminoepoxides have to be considered. Two pathways are examined for hydrolysis of β-acetoxyimines: cyclisation to oxazolones or conversion to acylglycinates when imines are converted to the isomeric enamines prior to deprotection.
Databáze:	OpenAIRE
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