Synthesis of chiral amino acid-derived nitrones and 1,3-dipolar cycloadditions with acrylic acid methyl ester

Authors
Blanarikova, I Fisera, L Kopanicakova, Z Salanski, P Jurczak, J Hametner, C
Citation
I. Blanarikova et al., Synthesis of chiral amino acid-derived nitrones and 1,3-dipolar cycloadditions with acrylic acid methyl ester, ARKIVOC, 2, 2001, pp. NIL_54-NIL_62
Citations number
25
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
ARKIVOC → ACNP
Volume
2
Year of publication
2001
Part
3
Pages
NIL_54 - NIL_62
Database
ISI
SICI code
Abstract
The chiral nitrones derived from alpha -amino acids react with acrylic acid methyl ester to afford the corresponding diastereomeric isoxazolidines 9a- d. The major products are in the C-3/C-4 erythro- and C-3/C-3a trans-config uration. The nitrones 3-8 were prepared from the corresponding alpha -amino aldehydes, starting from L-phenylalanine and L-valine.