RT info:eu-repo/semantics/article
T1 The organocatalyzed domino Michael–aldol reaction revisited. Synthesis of enantioenriched 3-hydroxycyclohexanone derivatives by reaction of enals with α,α′-diaryl-substituted acetone
A1 Guevara Pulido, James Oswaldo
A1 Andrés García, José María
A1 Pedrosa Sáez, Rafael
K1 Química orgánica
AB 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.
PB Royal Society of Chemistry
SN 2046-2069
YR 2015
FD 2015
LK http://uvadoc.uva.es/handle/10324/21451
UL http://uvadoc.uva.es/handle/10324/21451
LA eng
NO RSC Advances, 2015, 5, p. 65975-65981
NO Producción Científica
DS UVaDOC
RD 23-abr-2024