a-Methylserinals as an access to a-methyl-ß-hydroxyamino acids: Application in the synthesis of all stereoisomers of a- methylthreonine
- Avenoza, A. 1
- Busto, J.H. 1
- Corzana, F. 1
- Peregrina, J.M. 1
- Sucunza, D. 1
- Zurbano, M.M. 1
-
1
Universidad de La Rioja
info
ISSN: 0957-4166
Año de publicación: 2004
Volumen: 15
Número: 4
Páginas: 719-724
Tipo: Artículo
beta Ver similares en nube de resultadosOtras publicaciones en: Tetrahedron: Asymmetry
Resumen
The asymmetric synthesis of all stereoisomers of α-methylthreonine using a stereodivergent synthetic route starting from (S)- and (R)-N-Boc-N,O-isopropylidene-α-methylserinals is reported. The key step involves the asymmetric addition of methylmagnesium bromide to these aldehydes with a high level of asymmetric induction being observed. This methodology represents a powerful tool for the synthesis of different β-substituted α-methylserines. © 2003 Elsevier Ltd. All rights reserved.