6533b839fe1ef96bd12a650d
RESEARCH PRODUCT
Advances towards highly active and stereoselective simple and cheap proline-based organocatalysts
Michelangelo GruttadauriaPaola AgrigentoFrancesco GiacaloneRenato NotoPaolo Lo Meosubject
inorganic chemicalsChemistryorganic chemicalsOrganic ChemistryEnantioselective synthesisCyclohexanoneAsymmetric catalysiSettore CHIM/06 - Chimica OrganicaCyclopentanoneCatalysisEnaminechemistry.chemical_compoundOrganocatalysiAldol reactionOrganocatalysisAldol reactionOrganic chemistryWater chemistryAldol condensationPhysical and Theoretical Chemistrydescription
Ten 4-acyloxy-L-prolines were screened as catalysts at loadings of 2–0.1 mol-% for the direct asymmetric aldol reaction in water by using variable amounts of water. Among them, a new catalyst, the L-proline carrying a trans-4-(2,2-diphenylacetoxy) group, and a catalyst previously synthesized by us, the L-proline carrying a trans-4-(4-phenylbutanoyloxy) group, were found to be excellent catalysts for the aldol reaction between cyclohexanone or cyclopentanone and substituted benzaldehydes when employed in only 1 and 0.5 mol-%,respectively, at room temperature without additives. For such catalysts, high turnover numbers were obtained, which are among the highest values obtained for enamine organocatalysis. Finally, these catalysts can be synthesized by direct O-acylation from inexpensive molecules and successfully used in scaled-up reactions.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2010-08-24 |