Asymmetric synthesis of meso- and (2R, 4R)-2,4-diaminoglutaric acids

In order to synthesize meso- and (2R,4R)-2,4-diaminoglutaric acids, a synthetic route has been developed starting from Garner's aldehyde and where the key steps are the asymmetric hydrogenations of (E)- and (Z)-(R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-[2'-(benzamido)-2' -(methoxycarbo...

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Detalles Bibliográficos
Autores: Avenoza, A. [0000-0002-5465-3555], Cativiela, C., Peregrina, J.M. [0000-0003-3778-7065], Zurbano, M.M. [0000-0001-6370-3537]
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:1997
País:España
Institución:Universidad de La Rioja (UR)
Repositorio:RIUR. Repositorio Institucional de la Universidad de La Rioja
OAI Identifier:oai:portal.dialnet.es:doc/5bbc68feb750603269e8131d
Acceso en línea:https://investigacion.unirioja.es/documentos/5bbc68feb750603269e8131d
Access Level:acceso abierto
Descripción
Sumario:In order to synthesize meso- and (2R,4R)-2,4-diaminoglutaric acids, a synthetic route has been developed starting from Garner's aldehyde and where the key steps are the asymmetric hydrogenations of (E)- and (Z)-(R)-3-tert-butoxycarbonyl-2,2-dimethyl-4-[2'-(benzamido)-2' -(methoxycarbonyl)ethenyl]-1,3-oxazolidine, under heterogeneous conditions, followed by oxidation and further hydrolysis. A model is proposed to explain the stereochemical outcome of the asymmetric hydrogenation.