Synthesis of enantiomerically pure constrained gamma-hydroxy-alfa-amino acids by directed hydroxylation

  1. Avenoza, A. 2
  2. Cativiela, C. 1
  3. París, M. 2
  4. Peregrina, J.M. 2
  5. Saenz-Torre, B. 2
  1. 1 Instituto de Nanociencia y Materiales de Aragón
    info

    Instituto de Nanociencia y Materiales de Aragón

    Zaragoza, España

    ROR https://ror.org/031n2c920

  2. 2 Universidad de La Rioja
    info

    Universidad de La Rioja

    Logroño, España

    ROR https://ror.org/0553yr311

Revista:
Tetrahedron: Asymmetry

ISSN: 0957-4166

Año de publicación: 1997

Volumen: 8

Número: 7

Páginas: 1123-1129

Tipo: Artículo

DOI: 10.1016/S0957-4166(97)00083-9 SCOPUS: 2-s2.0-0030897809 WoS: WOS:A1997WV29000026 GOOGLE SCHOLAR

Otras publicaciones en: Tetrahedron: Asymmetry

Repositorio institucional: lock_openAcceso abierto Editor

Resumen

Efficient synthetic routes to enantiomerically pure (1R,3R,6R)- and (1S,3S,6S)-1-amino-3-hydroxy-6-phenylcyclohexane-1- carboxylic acids have been developed. The key step is a directed hydroxylation through an iodo-initiated O-functionalization reaction of methyl (1S,6R)- and (1R,6S)-1-aminocarbonyl-6-phenyl-3-cyclohexene-1- carboxylates, which can easily be obtained from the asymmetric Diels-Alder reactions of 1,3-butadiene with the (E)-2-cyanocinnamates of (S)-ethyl lactate and (R)-pantolactone, respectively.