Tandem reactions in self-sorted catalytic molecular hydrogels

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 catalyti...

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Bibliographic Details
Published in:Chemical science (Cambridge) 2016-01, Vol.7 (8), p.5568-5572
Main Authors: Singh, Nishant, Zhang, Kai, Angulo-Pachón, César A, Mendes, Eduardo, van Esch, Jan H, Escuder, Beatriu
Format: Article
Language:English
Subjects:
Carboxylic acids
Cascade chemical reactions
Catalysis
Catalysts
Hydrogels
Proline
Separation
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Summary: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. We report the orthogonal assembly of two structurally dissimilar catalytic hydrogelators with mutually incompatible functional groups able to retain their individual catalytic activity and thus catalyse tandem reactions in one pot.
ISSN:2041-6520
2041-6539
DOI:10.1039/c6sc01268j