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Enantioselective synthesis of (–)-chloramphenicol via silver-catalysed asymmetric isocyanoacetate aldol reaction

The highly enantio- and diastereoselective aldol reaction of isocyanoacetates catalysed by Ag(2)O and cinchona-derived amino phosphines applied to the synthesis of (–)- and (+)-chloramphenicol is described. The concise synthesis showcases the utility of this catalytic asymmetric methodology for the...

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Detalles Bibliográficos
Autores principales: Franchino, Allegra, Jakubec, Pavol, Dixon, Darren J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Royal Society of Chemistry 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4756631/
https://www.ncbi.nlm.nih.gov/pubmed/26510469
http://dx.doi.org/10.1039/c5ob02141c
Descripción
Sumario:The highly enantio- and diastereoselective aldol reaction of isocyanoacetates catalysed by Ag(2)O and cinchona-derived amino phosphines applied to the synthesis of (–)- and (+)-chloramphenicol is described. The concise synthesis showcases the utility of this catalytic asymmetric methodology for the preparation of bioactive compounds possessing α-amino-β-hydroxy motifs.