STEREOSELECTIVE SYNTHESIS OF ALPHA-HYDROXY-BETA-AMINO ACIDS USING D-GLYCERALDEHYDE AS THE HOMOCHIRAL SOURCE

Authors
CATIVIELA C DIAZDEVILLEGAS MD GALVEZ JA
Citation
C. Cativiela et al., STEREOSELECTIVE SYNTHESIS OF ALPHA-HYDROXY-BETA-AMINO ACIDS USING D-GLYCERALDEHYDE AS THE HOMOCHIRAL SOURCE, Tetrahedron : asymmetry, 7(2), 1996, pp. 529-536
Citations number
45
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Inorganic & Nuclear","Chemistry Physical
Journal title
Tetrahedron : asymmetry → ACNP
ISSN journal
09574166
Volume
7
Issue
2
Year of publication
1996
Pages
529 - 536
Database
ISI
SICI code
0957-4166(1996)7:2<529:SSOAAU>2.0.ZU;2-Z
Abstract
A systematic study of the diastereoselective addition of methyl organo metallic compounds to the benzyl imine derived from conveniently prote cted D-glyceraldehyde in order to develop a new approach to enantiomer ically pure alpha-hydroxy-beta-amino acids is reported. Methylmagnesiu m bromide addition afforded the corresponding adduct, which can be fur ther elaborated to give (2S, 3R) 3-amino-2-hydroxybutanoic acid, with complete diastereoselectivity.