Enantioselective organocatalytic Michael additions of aldehydes to enones with imidazolidinones: cocatalyst effects and evidence for an enamine intermediate.
J Am Chem Soc
; 127(33): 11598-9, 2005 Aug 24.
Article
em En
| MEDLINE
| ID: mdl-16104725
An enantioselective intermolecular Michael addition of aldehydes to enones catalyzed by imidazolidinones has been achieved. Chemoselectivity (Michael addition vs aldol) can be controlled through judicious choice of hydrogen-bond-donating cocatalysts. The optimal imidazolidinone/hydrogen-bond-donor pair affords Michael addition products in excess of 90% ee. Furthermore, we have isolated and characterized an enamine intermediate and demonstrated its efficacy as a nucleophile in the observed Michael addition reactions.
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Base de dados:
MEDLINE
Assunto principal:
Compostos Organometálicos
/
Imidazolidinas
/
Aldeídos
/
Aminas
/
Cetonas
Idioma:
En
Revista:
J Am Chem Soc
Ano de publicação:
2005
Tipo de documento:
Article
País de afiliação:
Estados Unidos