Stereoselective synthesis of γ-hydroxynorvaline through combination of organo- and biocatalysis.
Chem Commun (Camb)
; 50(99): 15669-72, 2014 Dec 25.
Article
em En
| MEDLINE
| ID: mdl-25251725
ABSTRACT
An efficient route for the synthesis of all four diastereomers of PMP-protected α-amino-γ-butyrolacton to access γ-hydroxynorvaline was established. The asymmetric key steps comprise an organocatalytic Mannich reaction and an enzymatic ketone reduction. Three reaction steps could be integrated in a one-pot process, using 2-PrOH both as solvent and as reducing agent. The sequential construction of stereogenic centres gave access to each of the four stereoisomers in high yield and with excellent stereocontrol.
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1
Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Valina
Idioma:
En
Revista:
Chem Commun (Camb)
Ano de publicação:
2014
Tipo de documento:
Article