A deep cavitand catalyzes the Diels-Alder reaction of bound maleimides.
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.
Hooley
Richard J
RJ
The Skaggs Institute for Chemical Biology, and the Department of Chemistry, The Scripps Research Institute, La Jolla, CA 92037, USA.
Rebek
Julius
J
D002384:Catalysis; D003500:Cyclization; D004988:Ethers, Cyclic / Q000737:chemistry*; D006860:Hydrogen Bonding; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D008301:Maleimides / Q000737:chemistry*; D008956:Models, Chemical; D008958:Models, Molecular; D011522:Protons; D012118:Resorcinols / Q000737:chemistry*
D004988:Ethers, Cyclic; D008301:Maleimides; D011522:Protons; D012118:Resorcinols; C442939:cavitand