Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 13, Issue 28, Pages 7711-7719Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/c5ob00937e
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Funding
- Dutch Ministry of Education, Culture and Science [024.001.035]
- European Research Council [246829]
- Netherlands Organisation for Scientific research (NWO - VENI) [700.10.406]
- European Union [293788]
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A water-soluble benzene-1,3,5-tricarboxamide (BTA) derivative that self-assembles into one-dimensional, helical, supramolecular polymers is functionalised at the periphery with one L-proline moiety. In water, the BTA-derivative forms micrometre long supramolecular polymers, which are stabilised by hydrophobic interactions and directional hydrogen bonds. Furthermore, we co-assemble a catalytically inactive, but structurally similar, BTA with the L-proline functionalised BTA to create co-polymers. This allows us to assess how the density of the L-proline units along the supramolecular polymer affects its activity and selectivity. Both the supramolecular polymers and co-polymers show high activity and selectivity as catalysts for the aldol reaction in water when using p-nitrobenzaldehyde and cyclohexanone as the substrates for the aldol reaction. After optimisation of the reaction conditions, a consistent conversion of 92 +/- 7%, de(anti) of 92 +/- 3%, and ee(anti) of 97 +/- 1% are obtained with a concentration of L-proline as low as 1 mol%.
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