Organic & Biomolecular Chemistry · 2008 · 31 citations · 33 references
Natural SciencesChemical EngineeringChemistryBiocatalysisCatalysisOrganic ChemistryAddition ReactionsCatalyst SynthesisConjugation ReactionsHeterocyclic ChemistryHeterocyclic CompoundsOrganic SynthesisBifunctional CatalysisBifunctional CatalystsChiral Catalyst DesignConjugate AdditionEnantioselective CatalysisEnantioselective Catalyst DesignEnantioselective SynthesisMolecular Catalysts
Guanidinyl pyrrolidines derived from 'S'-proline are effective catalysts for the enantioselective conjugate addition of malonate, nitroalkane and other carbon and heteroatom nucleophiles to cyclohexenone and cyclopentenone in the absence of basic additives. The stereoselectivity is strongly dependent on catalyst loading as well as reaction concentration.
33