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RESEARCH PRODUCT
The role of Zn2+ in enhancing the rate and stereoselectivity of the aldol reactions catalyzed by the simple prolinamide model
Gregorio AsensioCecilia Andreusubject
chemistry.chemical_classificationNucleophilic additionOrganic ChemistryBiochemistryAldehydeCombinatorial chemistryCatalysisEnaminechemistry.chemical_compoundchemistryAldol reactionDrug DiscoveryOrganic chemistryStereoselectivityAmine gas treatingLewis acids and basesdescription
Abstract The aldol reaction between acetone and 4-nitrobenzaldehyde catalyzed by single l -prolinamide and its zinc complexes has been studied. An increase in the rate and the stereoselectivity of the reaction has been shown by using zinc derivatives. A mechanistic proposal, based on NMR and ESI studies, has been put forward to explain the experimental data: zinc–prolinamide complexes catalyze the reaction following the general mechanism of stereoselective enamine nucleophilic addition to the acceptor aldehyde. Zn2+ prevents the nonspecific base-catalyzed reaction by diminishing the basicity of the amine nitrogen of prolinamide.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2011-09-01 | Tetrahedron |