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Producción CientíficaThe 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.Ministerio de Economía, Industria y Competitividad (CTQ 2011-28487)Junta de Castilla y León (programa de apoyo a proyectos de investigación – Ref. VA064U13)Universidad de Valladolid for a pre-doctoral fellowship

rsc advances

The organocatalyzed domino Michael–aldol reaction revisited. Synthesis of enantioenriched 3-hydroxycyclohexanone derivatives by reaction of enals with α,α′-diaryl-substituted acetone