Triggering Activity of Catalytic Rod‐Like Supramolecular Polymers |
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| Authors: | Dr. Elisa Huerta M. Sc. Bas van Genabeek Brigitte A. G. Lamers Dr. Marcel M. E. Koenigs Prof. Dr. E. W. Meijer Dr. Ir. Anja R. A. Palmans |
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| Affiliation: | Institute for Complex Molecular Systems, Eindhoven University of Technology, P.O. Box 513, 5600 MB Eindhoven (The Netherlands) |
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| Abstract: | Supramolecular polymers based on benzene‐1,3,5‐tricarboxamides (BTAs) functionalized with an L ‐ or D ‐proline moiety display high catalytic activity towards aldol reactions in water. High turnover frequencies (TOF) of up to 27×10?4 s?1 and excellent stereoselectivities (up to 96 % de, up to 99 % ee) were observed. In addition, the catalyst could be reused and remained active at catalyst loadings and substrate concentrations as low as 0.1 mol % and 50 mM , respectively. A temperature‐induced conformational change in the supramolecular polymer triggers the high activity of the catalyst. The supramolecular polymer’s helical sense in combination with the configuration of the proline (L ‐ or D ‐) is responsible for the observed selectivity. |
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| Keywords: | aldol reaction organocatalysis proline self‐assembly supramolecular polymers |
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