Triggering Activity of Catalytic Rod-Like Supramolecular Polymers

被引：35

作者：

Huerta, Elisa ^{[1
]}

van Genabeek, Bas ^{[1
]}

Lamers, Brigitte A. G. ^{[1
]}

Koenigs, Marcel M. E. ^{[1
]}

Meijer, E. W. ^{[1
]}

Palmans, Anja R. A. ^{[1
]}

机构：

[1] Eindhoven Univ Technol, Inst Complex Mol Syst, NL-5600 MB Eindhoven, Netherlands

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2015年 / 21卷 / 09期

基金：

欧洲研究理事会;

关键词：

aldol reaction; organocatalysis; proline; self-assembly; supramolecular polymers; ASYMMETRIC ALDOL REACTIONS; L-PROLINE; WATER; CONSEQUENCES; DIPEPTIDE;

D O I：

10.1002/chem.201405410

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：3682 / 3690

页数：9

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