Issue 8, 2016

Tandem reactions in self-sorted catalytic molecular hydrogels

Abstract

By equipping mutually incompatible carboxylic acid and proline catalytic groups with different self-assembling motives we have achieved self-sorting of the resulting catalytic gelators, namely SucVal8 and ProValDoc, into different supramolecular fibers, thus preventing the acidic and basic catalytic groups from interfering with each other. The resulting spatial separation of the incompatible catalytic functions is found to be essential to achieve one-pot deacetalization–aldol tandem reactions with up to 85% efficiency and 90% enantioselectivity. On the contrary, when SucVal8 was co-assembled with a structurally similar catalytically active hydrogelator (ProVal8), self-sorting was precluded and no tandem catalysis was observed.

Graphical abstract: Tandem reactions in self-sorted catalytic molecular hydrogels

Supplementary files

Article information

Article type
Edge Article
Submitted
21 Mar 2016
Accepted
06 May 2016
First published
09 May 2016
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2016,7, 5568-5572

Tandem reactions in self-sorted catalytic molecular hydrogels

N. Singh, K. Zhang, C. A. Angulo-Pachón, E. Mendes, J. H. van Esch and B. Escuder, Chem. Sci., 2016, 7, 5568 DOI: 10.1039/C6SC01268J

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