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

Authors
Avenoza, A Busto, JH Cativiela, C Peregrina, JM
Citation
A. Avenoza et al., Synthesis of conformationally constrained hydroxy-alpha-amino acids by intramolecular conjugate addition, AMINO ACIDS, 18(2), 2000, pp. 117-127
Citations number
19
Categorie Soggetti
Biochemistry & Biophysics
Journal title
AMINO ACIDS
ISSN journal
09394451 → ACNP
Volume
18
Issue
2
Year of publication
2000
Pages
117 - 127
Database
ISI
SICI code
0939-4451(2000)18:2<117:SOCCHA>2.0.ZU;2-E
Abstract
An efficient and easily applicable method for the synthesis of a variety of hydroxy-alpha-amino acids analogues of serine and phenylalanine has been e stablished. The method involves the stereoselective intramolecular conjugat e addition of the benzamide group to cyclohexenone promoted by Lewis acid. Subsequent transformations of functional groups provide the conformationall y constrained 2-hydroxy- and 2,4-dihydroxy-6-phenylcyclohexane-alpha-amino acids.