Asymmetric multicomponent domino reactions and highly enantioselective conjugated addition of thiols to alpha,beta-unsaturated aldehydes.
J Am Chem Soc
; 127(45): 15710-1, 2005 Nov 16.
Article
em En
| MEDLINE
| ID: mdl-16277506
ABSTRACT
An organocatalytic asymmetric multicomponent domino and a conjugated addition reaction to alpha,beta-unsaturated aldehydes are presented. The development is based, first, on an organocatalyzed highly enantioselective nucleophilic thiol addition to the beta-carbon atom in the iminium ion intermediate, followed by an electrophilic amination of the alpha-carbon atom to the enamine intermediate. The multicomponent reactions proceed to give enantiopure amino-thiols in moderate to good yields. Furthermore, the organocatalyzed thiol addition to alpha,beta-unsaturated aldehydes takes place in good yields and excellent enantioselectivities.
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01-internacional
Base de dados:
MEDLINE
Idioma:
En
Ano de publicação:
2005
Tipo de documento:
Article