2024-03-29T05:55:58Zhttps://uvadoc.uva.es/oai/requestoai:uvadoc.uva.es:10324/214512021-06-24T07:42:21Zcom_10324_1187com_10324_931com_10324_894com_10324_28542com_10324_952col_10324_1408col_10324_28543
Guevara Pulido, James Oswaldo
Andrés García, José María
Pedrosa Sáez, Rafael
2016-12-05T13:32:46Z
2016-12-05T13:32:46Z
2015
RSC Advances, 2015, 5, p. 65975-65981
2046-2069
http://uvadoc.uva.es/handle/10324/21451
10.1039/C5RA11215J
65975
5
65981
RSC Advances
The reaction of enals with α,α′-diaryl-substituted acetones (pKa > 18) catalyzed by (S)-1-(2-pyrrolidinylmethyl) pyrrolidine provides direct access to enantioenriched 2,5,6-trisubstituted-3-hydroxy cyclohexanones. The process constitutes a highly stereoselective organocatalytic tandem Michael-intramolecular aldol reaction. It has been demonstrated that the stereoselection is dependent on the reaction conditions because only syn diastereoisomers are able to cyclize, and that anti diastereoisomers participate in a retro-Michael process decreasing the enantioselection.
eng
info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by-nc-nd/4.0/
Attribution-NonCommercial-NoDerivatives 4.0 International
Química orgánica
The organocatalyzed domino Michael–aldol reaction revisited. Synthesis of enantioenriched 3-hydroxycyclohexanone derivatives by reaction of enals with α,α′-diaryl-substituted acetone
info:eu-repo/semantics/article