Synthesis of conformationally constrained hydroxy-alfa-amino acids by intramolecular conjugate addition

  1. Avenoza, A. 1
  2. Busto, J.H. 1
  3. Cativiela, C. 2
  4. Peregrina, J.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:
Amino Acids

ISSN: 0939-4451

Any de publicació: 2000

Volum: 18

Número: 2

Pàgines: 117-127

Tipus: Article

PMID: 10817404 SCOPUS: 2-s2.0-0034066185 WoS: WOS:000086343700002 GOOGLE SCHOLAR

Altres publicacions en: Amino Acids

Repositori institucional: lock_openAccés obert Editor

Resum

An efficient and easily applicable method for the synthesis of a variety of hydroxy-α-amino acids analogues of serine and phenylalanine has been established. The method involves the stereoselective intramolecular conjugate addition of the benzamide group to cyclohexenone promoted by Lewis acid. Subsequent transformations of functional groups provide the conformationally constrained 2-hydroxy- and 2,4-dihydroxy-6-phenylcyclohexane-α-amino acids.