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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.

SUBMITTER: Singh N

PROVIDER: S-EPMC6021788 | biostudies-other | 2016 Aug

REPOSITORIES: biostudies-other

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Tandem reactions in self-sorted catalytic molecular hydrogels.

Singh Nishant N Zhang Kai K Angulo-Pachón César A CA Mendes Eduardo E van Esch Jan H JH Escuder Beatriu B

Chemical science 20160509 8

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 <b>SucVal8</b> and <b>ProValDoc</b>, 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 tande ...[more]

PMID: 30034697

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