Abstract
The development of a performant aminated catalyst for aldol condensations requires the combined tuning of the active site, support and solvent system. For this purpose, a pyrrolidine group was immobilized on a swellable polymer resin. Favorable interactions between the support and water (in its role as solvent) resulted in a turnover frequency (TOF) amounting to 3.0 ± 1.5 × 10−3 s−1, despite potential inhibition of the active sites by formation of iminium species. The affinity of the solvent for the poly[(ethylene glycol) methacrylate] support resulted in efficient swelling of the catalytic material, which was shown to be key to the observed catalytic performance.
Funder
Special Research fund (BOF) of Ghent University
Research Foundation—Flanders
Hercules Foundation
Flemish Government
European Research Council
Subject
Physical and Theoretical Chemistry,Catalysis,General Environmental Science
Reference57 articles.
1. Biesemans, B., De Clercq, J., Stevens, C.V., Thybaut, J.W., and Lauwaert, J. (2022). Recent advances in amine catalyzed aldol condensations. Catal. Rev., 1–83.
2. Proline-Catalyzed Direct Asymmetric Aldol Reactions;J. Am. Chem. Soc.,2000
3. The Catalytic Asymmetric Aldol Reaction;Angew. Chem. Int. Ed.,2000
4. Hajos, Z.G., and Parrish, D.R. (1971). Asymmetric Synthesis of Organic Compounds. (US3975440A), U.S. Patent and Trademark Office.
5. New Type of Asymmetric Cyclization to Optically Active Steroid CD Partial Structures;Angew. Chem. Int. Ed.,1971
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