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Amino Acids

, Volume 18, Issue 2, pp 117–127 | Cite as

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

  • A. Avenoza
  • J. H. Busto
  • C. Cativiela
  • J. M. Peregrina

Summary.

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 pro-vide the conformationally constrained 2-hydroxy- and 2,4-dihydroxy-6-phenylcyclohexane-α-amino acids.

Keywords: Amino acids – 5(4H)-Oxazolone – Diels-Alder reaction – Intramolecular conjugate addition – Hydroxy-α-amino acids 

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Copyright information

© Springer-Verlag Wien 2000

Authors and Affiliations

  • A. Avenoza
    • 1
  • J. H. Busto
    • 1
  • C. Cativiela
    • 2
  • J. M. Peregrina
    • 1
  1. 1.Departamento de Química, Universidad de La Rioja, Logroño, SpainES
  2. 2.Departamento de Química Orgánica, Instituto de Ciencia de Materiales de Aragón, Universidad de Zaragoza-C.S.I.C, Zaragoza, SpainES

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