Issue 22, 2007
From the journal:

Organic & Biomolecular Chemistry

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

Richard J. Hooleya  and  Julius Rebek Jr.*a  

* Corresponding authors

a The Skaggs Institute for Chemical Biology and the Department of Chemistry, The Scripps Research Institute, La Jolla, CA, USA
E-mail: jrebek@scripps.edu
Fax: +1 858.784.2876
Tel: +1 858.784.2250

Abstract

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.

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

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Article information

DOI
https://doi.org/10.1039/B713104F
Article type
Paper
Submitted
28 Aug 2007
Accepted
21 Sep 2007
First published
04 Oct 2007

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

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

R. J. Hooley and J. Rebek Jr., Org. Biomol. Chem., 2007, 5, 3631 DOI: 10.1039/B713104F

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