Synthesis of conformationally constrained hydroxy-alfa-amino acids by intramolecular conjugate addition
- Avenoza, A. 1
- Busto, J.H. 1
- Cativiela, C. 2
- Peregrina, J.M. 1
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1
Universidad de La Rioja
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2
Instituto de Nanociencia y Materiales de Aragón
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ISSN: 0939-4451
Année de publication: 2000
Volumen: 18
Número: 2
Pages: 117-127
Type: Article
D'autres publications dans: Amino Acids
Résumé
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.