Cucurbit[7]uril as a Supramolecular Artificial Enzyme for Diels-Alder Reactions.
Angew Chem Int Ed Engl
; 56(49): 15688-15692, 2017 12 04.
Article
em En
| MEDLINE
| ID: mdl-29048713
The ability to mimic the activity of natural enzymes using supramolecular constructs (artificial enzymes) is a vibrant scientific research field. Herein, we demonstrate that cucurbit[7]uril (CB[7]) can catalyse Diels-Alder reactions for a number of substituted and unreactive N-allyl-2-furfurylamines under biomimetic conditions, without the need for protecting groups, yielding powerful synthons in previously unreported mild conditions. CB[7] rearranges the substrate in a highly reactive conformation and shields it from the aqueous environment, thereby mimicking the mode of action of a natural Diels-Alderase. These findings can be directly applied to the phenomenon of product inhibition observed in natural Diels-Alderase enzymes, and pave the way toward the development of novel, supramolecular-based green catalysts.
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MEDLINE
Assunto principal:
Hidrocarbonetos Aromáticos com Pontes
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Imidazóis
Idioma:
En
Ano de publicação:
2017
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Article