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Triggering activity of catalytic rod-like supramolecular polymers

By E Elisa Huerta Martinez, B Bas van Genabeek, BAG Brigitte Lamers, MME Marcel Koenigs, EW Bert Meijer and ARA Anja Palmans

Abstract

\u3cp\u3eSupramolecular 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\u3csup\u3e-4\u3c/sup\u3e s\u3csup\u3e-1\u3c/sup\u3e 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.\u3c/p\u3

Publisher: Wiley-VCH Verlag
Year: 2015
OAI identifier: oai:library.tue.nl:888258
Provided by: Repository TU/e
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