Turning Cucurbit[8]uril into a Supramolecular Nanoreactor for Asymmetric Catalysis

Lifei Zheng; Silvia Sonzini; Masyitha Ambarwati; Edina Rosta; Oren A. Scherman; Andreas Herrmann

doi:10.1002/anie.201505628

Turning Cucurbit[8]uril into a Supramolecular Nanoreactor for Asymmetric Catalysis

Lifei Zheng, Silvia Sonzini, Masyitha Ambarwati, Edina Rosta, Oren A. Scherman, Andreas Herrmann

Chemistry

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65 Citations (Scopus)

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Abstract

Chiral macromolecules have been widely used as synthetic pockets to mimic natural enzymes and promote asymmetric reactions. An achiral host, cucurbit[8]uril (CB[8]), was used for an asymmetric Lewis acid catalyzed Diels-Alder reaction. We achieved a remarkable increase in enantioselectivity and a large rate acceleration in the presence of the nanoreactor by using an amino acid as the chiral source. Mechanistic and computational studies revealed that both the amino acid-Cu²⁺ complex and the dienophile substrate are included inside the macrocyclic host cavity, suggesting that contiguity and conformational constraints are fundamental to the catalytic process and rate enhancement. These results pave the way towards new studies on asymmetric reactions catalyzed in confined achiral cavities.

Original language	English
Pages (from-to)	13007-13011
Number of pages	5
Journal	ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume	54
Issue number	44
Early online date	7 Sept 2015
DOIs	https://doi.org/10.1002/anie.201505628
Publication status	Published - 26 Oct 2015

Keywords

asymmetric catalysis
Diels-Alder reaction
host-guest systems
macrocycles
supramolecular chemistry

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Zheng_et_al-2015-Angewandte_Chemie_International_EditionFinal published version, 1.41 MBLicence: CC BY

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AU - Sonzini, Silvia

AU - Ambarwati, Masyitha

AU - Rosta, Edina

AU - Scherman, Oren A.

AU - Herrmann, Andreas

PY - 2015/10/26

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Turning Cucurbit[8]uril into a Supramolecular Nanoreactor for Asymmetric Catalysis

Abstract

Keywords

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