English   español  
Por favor, use este identificador para citar o enlazar a este item: http://hdl.handle.net/10261/19401
Compartir / Impacto:
Estadísticas
Add this article to your Mendeley library MendeleyBASE
Visualizar otros formatos: MARC | Dublin Core | RDF | ORE | MODS | METS | DIDL
Título

Highly stereoselective synthesis of stereochemically defined polyhydroxylated propargylamines by alkynylation of n-benzylimines derived from (R)-glyceraldehyde.

AutorDíez, Roberto; Badorrey, Ramón ; Díaz-de-Villegas, María D.; Gálvez, José A.
Palabras claveAmino alcohols
Asymmetric synthesis
Diastereoselectivity
Schiff bases
Nucleophilic addition
Fecha de publicación13-mar-2007
EditorWiley-VCH
CitaciónEuropean Journal of Organic Chemistry 2007(13): 2114 - 2120 (2007)
ResumenThe addition of the lithium derivative of tert-butyldimethylsilyl propargyl ether to N-benzylimines derived from (R)-2,3-O-isopropylideneglyceraldehyde has been achieved with acceptable yields and high diastereoselectivities. The syn/anti diastereoselectivity of the addition reaction can be controlled and reversed by the appropriate use of Lewis acids as imine precomplexing agents. Double stereodifferentiation processes using imines derived from (R)-2,3-O-isopropylideneglyceraldehyde and (R)- or (S)--methylbenzylamine as starting materials occur with total stereocontrol to afford syn and anti vic-propargylamino alcohol derivatives with orthogonally protected hydroxymethyl groups on both sides of the central core.(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)
Descripción7 pages, 2 schemes, 1 figure1 1 table.
Versión del editorhttp://dx.doi.org/10.1002/ejoc.200601011
URIhttp://hdl.handle.net/10261/19401
DOI10.1002/ejoc.200601011
Aparece en las colecciones: (ICMA) Artículos
Ficheros en este ítem:
No hay ficheros asociados a este ítem.
Mostrar el registro completo
 

Artículos relacionados:


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