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Cucurbit[7]uril as a Supramolecular Artificial Enzyme for Diels–Alder Reactions
Author(s) -
Palma Aniello,
Artelsmair Markus,
Wu Guanglu,
Lu Xiaoyong,
Barrow Steven J.,
Uddin Najib,
Rosta Edina,
Masson Eric,
Scherman Oren A.
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201706487
Subject(s) - supramolecular chemistry , synthon , supramolecular catalysis , enzyme , chemistry , natural product , artificial enzyme , aqueous solution , catalysis , substrate (aquarium) , combinatorial chemistry , biocatalysis , stereochemistry , organic chemistry , reaction mechanism , biology , molecule , ecology
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.