1-(Alpha-aminobenzyl)-2-naphthol: a new chiral auxiliary for the synthesis of enantiopure alpha-aminophosphonic acids.
Chemistry
; 15(27): 6718-22, 2009 Jul 06.
Article
en En
| MEDLINE
| ID: mdl-19479932
ABSTRACT
A new diastereoselective synthesis of alpha-aminophosphonates has been developed, based on the reaction, in the presence of trifluoroacetic acid, of trialkyl phosphites with chiral imines derived from (R)- or (S)-1-(alpha-aminobenzyl)-2-naphthol. The reaction proceeds at room temperature in toluene with high diastereoselectivity. The major diastereomer can be separated by crystallization from an appropriate solvent. The relative configuration of both chiral centers of the major diastereomer was determined by single-crystal X-ray structure analysis. The desired alpha-aminophosphonic acids can be obtained in enantiopure form by treatment of the corresponding diastereomers with HCl.
Texto completo:
1
Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
Organofosfonatos
/
Iminas
/
Naftoles
Idioma:
En
Revista:
Chemistry
Asunto de la revista:
QUIMICA
Año:
2009
Tipo del documento:
Article
País de afiliación:
Rusia