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Aggregation-Induced Catalysis: Asymmetric Catalysis with Chiral Aggregates

So far, there have been 4 methods to control chirality including the use of chiral auxiliaries, reagents, solvents, and catalysts documented in literature and textbooks. Among them, asymmetric catalysts are normally divided into homogeneous and heterogeneous catalysis. In this report, we present a n...

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Autores principales: Tang, Yao, Wang, Yu, Yuan, Qingkai, Zhang, Sai, Wang, Jia-Yin, Jin, Shengzhou, Xu, Ting, Pan, Junyi, Surowiec, Kazimierz, Li, Guigen
Formato: Online Artículo Texto
Lenguaje:English
Publicado: AAAS 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10254464/
https://www.ncbi.nlm.nih.gov/pubmed/37303602
http://dx.doi.org/10.34133/research.0163
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author Tang, Yao
Wang, Yu
Yuan, Qingkai
Zhang, Sai
Wang, Jia-Yin
Jin, Shengzhou
Xu, Ting
Pan, Junyi
Surowiec, Kazimierz
Li, Guigen
author_facet Tang, Yao
Wang, Yu
Yuan, Qingkai
Zhang, Sai
Wang, Jia-Yin
Jin, Shengzhou
Xu, Ting
Pan, Junyi
Surowiec, Kazimierz
Li, Guigen
author_sort Tang, Yao
collection PubMed
description So far, there have been 4 methods to control chirality including the use of chiral auxiliaries, reagents, solvents, and catalysts documented in literature and textbooks. Among them, asymmetric catalysts are normally divided into homogeneous and heterogeneous catalysis. In this report, we present a new type of asymmetric control—asymmetric catalysis via chiral aggregates that would not belong to the above categories. This new strategy is represented by catalytic asymmetric dihydroxylation reaction of olefins in which chiral ligands are aggregated by taking advantage of typical aggregation-induced emission systems containing tetrahydrofuran and H(2)O cosolvents. It was proven that the chiral induction can be enhanced from er of 78:22 to 97:3 simply by changing the ratios of these 2 cosolvents. The formation of chiral aggregates of asymmetric dihydroxylation ligands, (DHQD)(2)PHAL and (DHQ)(2)PHAL, has been proven by aggregation-induced emission and a new analytical tool—aggregation-induced polarization established by our laboratory. In the meanwhile, chiral aggregates were found to be formed either by adding NaCl into tetrahydrofuran/H(2)O systems or by increasing concentrations of chiral ligands. The present strategy also showed promising reverse control of enantioselectivity in the Diels–Alder reaction. This work is anticipated to be extended broadly to general catalysis, especially to asymmetric catalysis in the future.
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spelling pubmed-102544642023-06-10 Aggregation-Induced Catalysis: Asymmetric Catalysis with Chiral Aggregates Tang, Yao Wang, Yu Yuan, Qingkai Zhang, Sai Wang, Jia-Yin Jin, Shengzhou Xu, Ting Pan, Junyi Surowiec, Kazimierz Li, Guigen Research (Wash D C) Research Article So far, there have been 4 methods to control chirality including the use of chiral auxiliaries, reagents, solvents, and catalysts documented in literature and textbooks. Among them, asymmetric catalysts are normally divided into homogeneous and heterogeneous catalysis. In this report, we present a new type of asymmetric control—asymmetric catalysis via chiral aggregates that would not belong to the above categories. This new strategy is represented by catalytic asymmetric dihydroxylation reaction of olefins in which chiral ligands are aggregated by taking advantage of typical aggregation-induced emission systems containing tetrahydrofuran and H(2)O cosolvents. It was proven that the chiral induction can be enhanced from er of 78:22 to 97:3 simply by changing the ratios of these 2 cosolvents. The formation of chiral aggregates of asymmetric dihydroxylation ligands, (DHQD)(2)PHAL and (DHQ)(2)PHAL, has been proven by aggregation-induced emission and a new analytical tool—aggregation-induced polarization established by our laboratory. In the meanwhile, chiral aggregates were found to be formed either by adding NaCl into tetrahydrofuran/H(2)O systems or by increasing concentrations of chiral ligands. The present strategy also showed promising reverse control of enantioselectivity in the Diels–Alder reaction. This work is anticipated to be extended broadly to general catalysis, especially to asymmetric catalysis in the future. AAAS 2023-06-09 /pmc/articles/PMC10254464/ /pubmed/37303602 http://dx.doi.org/10.34133/research.0163 Text en Copyright © 2023 Yao Tang et al. https://creativecommons.org/licenses/by/4.0/Exclusive licensee Science and Technology Review Publishing House. No claim to original U.S. Government Works. Distributed under a Creative Commons Attribution License 4.0 (CC BY 4.0) (https://creativecommons.org/licenses/by/4.0/) .
spellingShingle Research Article
Tang, Yao
Wang, Yu
Yuan, Qingkai
Zhang, Sai
Wang, Jia-Yin
Jin, Shengzhou
Xu, Ting
Pan, Junyi
Surowiec, Kazimierz
Li, Guigen
Aggregation-Induced Catalysis: Asymmetric Catalysis with Chiral Aggregates
title Aggregation-Induced Catalysis: Asymmetric Catalysis with Chiral Aggregates
title_full Aggregation-Induced Catalysis: Asymmetric Catalysis with Chiral Aggregates
title_fullStr Aggregation-Induced Catalysis: Asymmetric Catalysis with Chiral Aggregates
title_full_unstemmed Aggregation-Induced Catalysis: Asymmetric Catalysis with Chiral Aggregates
title_short Aggregation-Induced Catalysis: Asymmetric Catalysis with Chiral Aggregates
title_sort aggregation-induced catalysis: asymmetric catalysis with chiral aggregates
topic Research Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10254464/
https://www.ncbi.nlm.nih.gov/pubmed/37303602
http://dx.doi.org/10.34133/research.0163
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