Efficient synthesis of enantiomerically pure beta2-amino acids via chiral isoxazolidinones.
J Org Chem
; 68(4): 1575-8, 2003 Feb 21.
Article
em En
| MEDLINE
| ID: mdl-12585907
ABSTRACT
We report a practical and scalable synthetic route for the preparation of alpha-substituted beta-amino acids (beta(2)-amino acids). Michael addition of a chiral hydroxylamine, derived from alpha-methylbenzylamine, to an alpha-alkylacrylate followed by cyclization gives a diastereomeric mixture of alpha-substituted isoxazolidinones. These diastereomers are separable by column chromatography. Subsequent hydrogenation of the purified isoxazolidinones followed by Fmoc protection affords enantiomerically pure Fmoc-beta(2)-amino acids, which are useful for beta-peptide synthesis. This route provides access to both enantiomers of a protected beta(2)-amino acid.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Aminoácidos
/
Isoxazóis
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2003
Tipo de documento:
Article
País de afiliação:
Estados Unidos