Asymmetric Michael reaction of aldehydes with ß-nitroalkenes catalyzed by pyrrolidine-camphor derived organocatalysts bearing hydrogen-bond donors.
Chirality
; 24(4): 271-5, 2012 Apr.
Article
en En
| MEDLINE
| ID: mdl-22278901
ABSTRACT
Several pyrrolidine-camphor derived organocatalysts were designed and synthesized. These organocatalysts were used for direct Michael reaction of aldehydes with nitroalkenes to give the desired γ-nitrocarbonyl compounds in high yields (up to 99%), high diastereoselectivities (synanti up to 928), and good to excellent enantioselectivities (up to 94% ee). Possible transition-state model was also proposed for this asymmetric transformation, which may involve hydrogen-bond interactions between the nucleophilic enamine formed in situ and the nitroalkenes.
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1
Bases de datos:
MEDLINE
Asunto principal:
Pirrolidinas
/
Alcanfor
/
Aldehídos
/
Alquenos
Idioma:
En
Revista:
Chirality
Asunto de la revista:
BIOLOGIA MOLECULAR
/
QUIMICA
Año:
2012
Tipo del documento:
Article