| Article ID | Journal | Published Year | Pages | File Type |
|---|---|---|---|---|
| 5221963 | Tetrahedron | 2011 | 7 Pages |
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.
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Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Cecilia Andreu, Gregorio Asensio,