English   español  
Por favor, use este identificador para citar o enlazar a este item: http://hdl.handle.net/10261/154736
COMPARTIR / IMPACTO:
Estadísticas
logo share SHARE logo core CORE   Add this article to your Mendeley library MendeleyBASE

Visualizar otros formatos: MARC | Dublin Core | RDF | ORE | MODS | METS | DIDL
Exportar a otros formatos:
Título

Synthesis of enantiomerically pure δ-benzylproline derivatives

AutorRodríguez-Díaz, Isabel ; Calaza, M. Isabel ; Jiménez, Ana I. ; Cativiela, Carlos
Fecha de publicación2015
EditorRoyal Society of Chemistry (Great Britain)
CitaciónNew Journal of Chemistry 39(5): 3310-3318 (2015)
ResumenThe (2S,5R) stereoisomer of 5-benzylproline, i.e. the l-proline analogue that bears a δ-benzyl substituent cis to the carbonyl function, has been prepared in enantiomerically pure form and excellent global yield. The procedure involves the construction of the pyrrolidine ring through intramolecular cyclization and uses as starting material the enantiopure β-amino acid obtained by homologation of l-phenylalanine. The generation of an intermediate vinyl triflate with full regiochemical control followed by a stereoselective hydrogenation reaction allowed the isolation of the target δ-substituted l-proline analogue in optically pure form and 43% overall yield from the initial β-amino acid. The trans stereoisomer of (2R,5R) configuration is obtained as a minor product through a less stereoselective hydrogenation reaction.
Versión del editorhttps://doi.org/10.1039/C4NJ01894J
URIhttp://hdl.handle.net/10261/154736
DOI10.1039/C4NJ01894J
Identificadoresdoi: 10.1039/C4NJ01894J
e-issn: 1369-9261
issn: 1144-0546
Aparece en las colecciones: (ISQCH) Artículos
Ficheros en este ítem:
Fichero Descripción Tamaño Formato  
enantiomerically.pdf1,49 MBAdobe PDFVista previa
Visualizar/Abrir
Mostrar el registro completo
 


NOTA: Los ítems de Digital.CSIC están protegidos por copyright, con todos los derechos reservados, a menos que se indique lo contrario.