期刊
CHEMISTRY-A EUROPEAN JOURNAL
卷 21, 期 9, 页码 3682-3690出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201405410
关键词
aldol reaction; organocatalysis; proline; self-assembly; supramolecular polymers
资金
- Netherlands Organisation for Scientific Research (NWO - TOP) [10007851]
- Dutch Ministry of Education, Culture and Science [024.001.035]
- European Research Council [246829]
- National Research School Catalysis (NRSC-C)
- Marie Curie Actions SCP-NANO [FP7-PEOPLE-2010-IEF-274668]
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 27x10(-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 0.1mol% and 50mM, 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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