A deep cavitand catalyzes the Diels–Alder reaction of bound maleimides

Richard J. Hooley; Julius Rebek Jr.

doi:10.1039/B713104F

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Organic & Biomolecular Chemistry

Issue 22, 2007

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A deep cavitand catalyzes the Diels–Alder reaction of bound maleimides

Richard J. Hooley and Julius Rebek Jr.

Org. Biomol. Chem., 2007, 5, 3631-3636

DOI: 10.1039/B713104F
Received 28 Aug 2007, Accepted 21 Sep 2007
First published on the web 04 Oct 2007

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Abstract
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A deep cavitand catalyzes Diels–Alder reactions of bound maleimides via activation of the dienophile by interaction with the organized hydrogen bonding network at the cavitand rim. Rapid in–out exchange of reactant and product allows efficient turnover. The increase in steric bulk of the reaction product lessens its binding affinity, reducing (and in some cases completely eliminating) product inhibition.

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Organic & Biomolecular Chemistry

A deep cavitand catalyzes the Diels–Alder reaction of bound maleimides

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