Publication

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

Zheng, L., Sonzini, S., Ambarwati, M., Rosta, E., Scherman, O. A. & Herrmann, A., 2015, In : Angewandte Chemie - International Edition. 54, 44, p. 13007-13011 5 p.

Research output: Contribution to journalArticleAcademicpeer-review

APA

Zheng, L., Sonzini, S., Ambarwati, M., Rosta, E., Scherman, O. A., & Herrmann, A. (2015). Turning Cucurbit[8]uril into a Supramolecular Nanoreactor for Asymmetric Catalysis. Angewandte Chemie - International Edition, 54(44), 13007-13011. https://doi.org/10.1002/anie.201505628

Author

Zheng, Lifei ; Sonzini, Silvia ; Ambarwati, Masyitha ; Rosta, Edina ; Scherman, Oren A ; Herrmann, Andreas. / Turning Cucurbit[8]uril into a Supramolecular Nanoreactor for Asymmetric Catalysis. In: Angewandte Chemie - International Edition. 2015 ; Vol. 54, No. 44. pp. 13007-13011.

Harvard

Zheng, L, Sonzini, S, Ambarwati, M, Rosta, E, Scherman, OA & Herrmann, A 2015, 'Turning Cucurbit[8]uril into a Supramolecular Nanoreactor for Asymmetric Catalysis', Angewandte Chemie - International Edition, vol. 54, no. 44, pp. 13007-13011. https://doi.org/10.1002/anie.201505628

Standard

Turning Cucurbit[8]uril into a Supramolecular Nanoreactor for Asymmetric Catalysis. / Zheng, Lifei; Sonzini, Silvia; Ambarwati, Masyitha; Rosta, Edina; Scherman, Oren A; Herrmann, Andreas.

In: Angewandte Chemie - International Edition, Vol. 54, No. 44, 2015, p. 13007-13011.

Research output: Contribution to journalArticleAcademicpeer-review

Vancouver

Zheng L, Sonzini S, Ambarwati M, Rosta E, Scherman OA, Herrmann A. Turning Cucurbit[8]uril into a Supramolecular Nanoreactor for Asymmetric Catalysis. Angewandte Chemie - International Edition. 2015;54(44):13007-13011. https://doi.org/10.1002/anie.201505628


BibTeX

@article{f7e0417ba6894edfbc244c353f5f7166,
title = "Turning Cucurbit[8]uril into a Supramolecular Nanoreactor for Asymmetric Catalysis",
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-Cu(2+) 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.",
author = "Lifei Zheng and Silvia Sonzini and Masyitha Ambarwati and Edina Rosta and Scherman, {Oren A} and Andreas Herrmann",
note = "{\circledC} 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.",
year = "2015",
doi = "10.1002/anie.201505628",
language = "English",
volume = "54",
pages = "13007--13011",
journal = "Angewandte Chemie - International Edition",
issn = "1433-7851",
publisher = "WILEY-V C H VERLAG GMBH",
number = "44",

}

RIS

TY - JOUR

T1 - Turning Cucurbit[8]uril into a Supramolecular Nanoreactor for Asymmetric Catalysis

AU - Zheng, Lifei

AU - Sonzini, Silvia

AU - Ambarwati, Masyitha

AU - Rosta, Edina

AU - Scherman, Oren A

AU - Herrmann, Andreas

N1 - © 2015 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the Creative Commons Attribution License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.

PY - 2015

Y1 - 2015

N2 - 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-Cu(2+) 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.

AB - 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-Cu(2+) 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.

U2 - 10.1002/anie.201505628

DO - 10.1002/anie.201505628

M3 - Article

C2 - 26383272

VL - 54

SP - 13007

EP - 13011

JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

SN - 1433-7851

IS - 44

ER -

ID: 25190454