Highly diastereoselective arylations of substituted piperidines.
J Am Chem Soc
; 133(13): 4774-7, 2011 Apr 06.
Article
en En
| MEDLINE
| ID: mdl-21388211
ABSTRACT
A highly diastereoselective methodology for the preparation of various substituted piperidines via Negishi cross-couplings with (hetero)aryl iodides was developed. Depending on the position of the C-Zn bond relative to the nitrogen (position 2 vs position 4), the stereoselectivity of the coupling can be directed toward either the trans- or cis-2,4-disubstituted products. Density functional theory calculations on the relative stabilities of the Zn and Pd intermediates were performed to explain the high diastereoselectivities obtained. A novel 1,2-migration of Pd further expands this method to the stereoselective preparation of 5-aryl-2,5-disubstituted piperidines.
Texto completo:
1
Colección:
01-internacional
Base de datos:
MEDLINE
Asunto principal:
Piperidinas
Idioma:
En
Revista:
J Am Chem Soc
Año:
2011
Tipo del documento:
Article
País de afiliación:
Alemania