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Cucurbit[7]uril as a Supramolecular Artificial Enzyme for Diels-Alder Reactions. | LitMetric

Cucurbit[7]uril as a Supramolecular Artificial Enzyme for Diels-Alder Reactions.

Angew Chem Int Ed Engl

Melville Laboratory for Polymer Synthesis Department of Chemistry, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, UK.

Published: December 2017

AI Article Synopsis

Article Abstract

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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Source
http://dx.doi.org/10.1002/anie.201706487DOI Listing

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