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

  1. Avenoza, A. 1
  2. Cativiela, C. 2
  3. Peregrina, J.M. 1
  4. Zurbano, M.M. 1
  1. 1 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

  2. 2 Instituto de Nanociencia y Materiales de Aragón
    info

    Instituto de Nanociencia y Materiales de Aragón

    Zaragoza, España

    ROR https://ror.org/031n2c920

Revista:
Tetrahedron: Asymmetry

ISSN: 0957-4166

Año de publicación: 1997

Volumen: 8

Número: 6

Páginas: 863-871

Tipo: Artículo

DOI: 10.1016/S0957-4166(97)00044-X SCOPUS: 2-s2.0-0031002763 WoS: WOS:A1997WQ93300015 GOOGLE SCHOLAR

Otras publicaciones en: Tetrahedron: Asymmetry

Repositorio institucional: lock_openAcceso abierto Editor

Resumen

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.