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Heterobifunctional Rotaxanes for Asymmetric Catalysis

Heterobifunctional rotaxanes serve as efficient catalysts for the addition of malonates to Michael acceptors. We report a series of four different heterobifunctional rotaxanes, featuring an amine‐based thread and a chiral 1,1′‐binaphthyl‐phosphoric‐acid‐based macrocycle. High‐level DFT calculations...

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Detalles Bibliográficos
Autores principales: Pairault, Noël, Zhu, Hui, Jansen, Dennis, Huber, Alexander, Daniliuc, Constantin G., Grimme, Stefan, Niemeyer, Jochen
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7154720/
https://www.ncbi.nlm.nih.gov/pubmed/31793163
http://dx.doi.org/10.1002/anie.201913781
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author Pairault, Noël
Zhu, Hui
Jansen, Dennis
Huber, Alexander
Daniliuc, Constantin G.
Grimme, Stefan
Niemeyer, Jochen
author_facet Pairault, Noël
Zhu, Hui
Jansen, Dennis
Huber, Alexander
Daniliuc, Constantin G.
Grimme, Stefan
Niemeyer, Jochen
author_sort Pairault, Noël
collection PubMed
description Heterobifunctional rotaxanes serve as efficient catalysts for the addition of malonates to Michael acceptors. We report a series of four different heterobifunctional rotaxanes, featuring an amine‐based thread and a chiral 1,1′‐binaphthyl‐phosphoric‐acid‐based macrocycle. High‐level DFT calculations provided mechanistic insights and enabled rational catalyst improvements, leading to interlocked catalysts that surpass their non‐interlocked counterparts in terms of reaction rates and stereoselectivities.
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spelling pubmed-71547202020-04-15 Heterobifunctional Rotaxanes for Asymmetric Catalysis Pairault, Noël Zhu, Hui Jansen, Dennis Huber, Alexander Daniliuc, Constantin G. Grimme, Stefan Niemeyer, Jochen Angew Chem Int Ed Engl Research Articles Heterobifunctional rotaxanes serve as efficient catalysts for the addition of malonates to Michael acceptors. We report a series of four different heterobifunctional rotaxanes, featuring an amine‐based thread and a chiral 1,1′‐binaphthyl‐phosphoric‐acid‐based macrocycle. High‐level DFT calculations provided mechanistic insights and enabled rational catalyst improvements, leading to interlocked catalysts that surpass their non‐interlocked counterparts in terms of reaction rates and stereoselectivities. John Wiley and Sons Inc. 2020-01-16 2020-03-23 /pmc/articles/PMC7154720/ /pubmed/31793163 http://dx.doi.org/10.1002/anie.201913781 Text en © 2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc/4.0/ License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited and is not used for commercial purposes.
spellingShingle Research Articles
Pairault, Noël
Zhu, Hui
Jansen, Dennis
Huber, Alexander
Daniliuc, Constantin G.
Grimme, Stefan
Niemeyer, Jochen
Heterobifunctional Rotaxanes for Asymmetric Catalysis
title Heterobifunctional Rotaxanes for Asymmetric Catalysis
title_full Heterobifunctional Rotaxanes for Asymmetric Catalysis
title_fullStr Heterobifunctional Rotaxanes for Asymmetric Catalysis
title_full_unstemmed Heterobifunctional Rotaxanes for Asymmetric Catalysis
title_short Heterobifunctional Rotaxanes for Asymmetric Catalysis
title_sort heterobifunctional rotaxanes for asymmetric catalysis
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7154720/
https://www.ncbi.nlm.nih.gov/pubmed/31793163
http://dx.doi.org/10.1002/anie.201913781
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