English   español  
Por favor, use este identificador para citar o enlazar a este item: http://hdl.handle.net/10261/15622
Título

On the regio- and stereoselective synthesis of aminocyclitols from cyclitol epoxides: the effect of Li as a chelating agent

AutorSerrano, Pedro; Llebaria, Amadeu; Vázquez, Jordi; Pablo, Joan de; Anglada Rull, Josep M.; Delgado Cirilo, Antonio
Palabras claveAb initio calculations
Amino alcohols
Conformation analysis
Epoxides
Regioselectivity
Fecha de publicación13-may-2005
EditorJohn Wiley & Sons
CitaciónChemistry: A European Journal 11(15): 4465-4472 (2005)
ResumenExperimental and theoretical studies on the influence of Li ions on the regio- and the stereoselectivity of the reaction of cyclitol epoxides with nitrogen nucleophiles have been carried out. Model studies with NaN3 as a nucleophile in the absence of Li ions predict a mixture of C1 and C2 regioadducts. The inclusion of two Li ions as a chelating agent favours the operation of a low populated all-axial conformation leading ultimately to the C1 adducts. In all cases, the results can be rationalised by geometric and energetic considerations of the corresponding transition states. Predictions of the theoretical calculations are in good agreement with the experimental results using primary and secondary amines as nucleophiles, and thus confirm the validity of this study.
Descripción8 pages, 3 figures, 1 table.-- PMID: 15892185 [PubMed].-- Printed version published Jul 18, 2005.
Corrigendum published in: Chemistry 12(2): 349 (Dec 2005), http://dx.doi.org/10.1002/chem.200690007
Versión del editorhttp://dx.doi.org/10.1002/chem.200401270
URIhttp://hdl.handle.net/10261/15622
DOI10.1002/chem.200401270
ISSN0947-6539 (Print)
1521-3765 (Online)
Aparece en las colecciones: (IQAC) 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.