Enantioselective recognition based on chiral macrocyclic hosts DOI Open Access

Qingyu Zhao,

Rong Fu,

Kang Cai

et al.

Scientia Sinica Chimica, Journal Year: 2023, Volume and Issue: 53(12), P. 2444 - 2459

Published: Sept. 10, 2023

Homochirality is a fundamental structural characteristic of biological systems. Therefore, the recognition and differentiation chiral enantiomers hold significant importance in various fields related to life health. Macrocyclic hosts serve as crucial tools for molecular recognition, construction macrocyclic enantiomeric guests has remained central topic supramolecular chemistry. In recent years, with vibrant development host-guest chemistry, progress been achieved enantioselective based on hosts. This article provides an overview common strategies constructing macrocycles, categorically reviews representative their capabilities, aiming stimulate application outstanding abilities. Finally, current challenges future prospects this field are summarized.

Language: Английский

Host–Guest Chemosensor Ensembles based on Water-Soluble Sulfonated Calix[n]arenes and a Pyranoflavylium Dye for the Optical Detection of Biogenic Amines DOI Creative Commons
Ana Sofia Pires,

Kevin Droguett Muñoz,

Víctor de Freitas

et al.

Journal of Agricultural and Food Chemistry, Journal Year: 2024, Volume and Issue: 72(7), P. 3719 - 3729

Published: Feb. 12, 2024

Biogenic amines (BAs) are biologically active nitrogen-containing compounds formed during the food spoilage process and often related as key markers of quality, safety, freshness. Because their presence in foods at high levels can cause significant health problems, researchers have been focused on developing novel strategies methods for early detection capture these analytes. Herein, water-soluble sulfonated calix[n]arene macrocycles (SC4, SC6, SC8) a pH-sensitive dye (4′-hydroxy-10-methylpyranoflavylium) were investigated host–guest systems BA sensing. The hosts able to bind flavylium cation with association constants 103 104 M–1. complexation also allowed tuning its pKa from 6.72 (free) toward values: 7.68 (SC4), 7.79 (SC6), 8.45 (SC8). These data crucial optimize complexes optical sensing putrescine/tyramine (pH 7.2–7.6), yielding colorimetric redshift yellow red. was demonstrated by fluorescence quenching calix[n]arene/dye recovery after addition BAs. 1H NMR spectroscopy used demonstrate interaction mode, confirming an encapsulation-driven mechanism. Overall, great potential BAs, one main spoilage.

Language: Английский

Citations

5
Recent applications of macrocycles in supramolecular catalysis DOI
Conghui Wang, Lei Xu, Zhenhua Jia

et al.

Chinese Chemical Letters, Journal Year: 2023, Volume and Issue: 35(4), P. 109075 - 109075

Published: Sept. 9, 2023

Language: Английский

Citations

13
Supramolecular Double-Helical Polymers: Supramolecular Chiral Induction and Asymmetric Catalysis DOI Creative Commons

Xiaojun Guo,

Xinyu Jia, Qin He

et al.

Molecules, Journal Year: 2025, Volume and Issue: 30(7), P. 1517 - 1517

Published: March 28, 2025

Seeking a supramolecular chiral system induced by trace molecules instead of traditional complex and expensive ligands to achieve high yield or ee value conversion the products is great significance in asymmetric synthesis but still remains challenge. Herein, two types double helical systems, (M)-Helix (P)-Helix, with opposite optics were constructed situ using tyrosine-functionalized pillar[5]arene as inducers. These systems exhibit chiroptical stability enable remarkable chirality amplification from 7 mol% seeds. When applied intermolecular olefin cyano-trifluoromethylation, exhibits catalytic efficiency (yield up 89%), whereas (P)-Helix achieves higher enantioselectivity (ee 84%). This research will provide new ideas for catalysts organic catalysis applications.

Language: Английский

Citations

0
Palladium-Catalyzed Aminosulfonylation of ortho-Iodoanilines with the Insertion of Sulfur Dioxide for the Synthesis of 3,4-Dihydro-benzothiadiazine 1,1-Dioxides DOI
Zhenjie Qi,

Simiaomiao Wen,

Hao Li

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(40), P. 7322 - 7326

Published: Oct. 4, 2023

A simple and efficient Pd-catalyzed oxidative cyclization system is developed for the chemo- regioselective synthesis of 3,4-dihydro-benzothiadiazine 1,1-dioxides, which are formed through aminosulfonylation ortho-iodoanilines with SO2. DABSO utilized as source SO2, organic compound O2 acts an oxidant. This direct C-S, S-N, C-N functionalization highly efficient, broad functional group tolerance observed, resulting in moderate to excellent yields 1,1-dioxides. Furthermore, this method amenable gram-scale synthesis.

Language: Английский

Citations

4
Construction of C–X (X = N, O) bonds from benzyl alcohols via Cu-BTC-catalyzed oxidative coupling DOI

Yujuan Wu,

Lianji Zhang,

Huimin Liu

et al.

Catalysis Science & Technology, Journal Year: 2024, Volume and Issue: 14(15), P. 4366 - 4375

Published: Jan. 1, 2024

Herein, an efficient and environmentally friendly Cu-BTC catalytic system is reported, which can be successfully applied to the oxidative coupling of benzyl alcohols for construction C–X (X = N, O) bonds.

Language: Английский

Citations

1
Continuous Flow Ni- or Ru-Zeolite-Catalyzed Intramolecular Dehydration of Diols and Seco-Acids for Macrocyclic Ethers and Lactones DOI

Dashrat Vishambar Sutar,

Akash Bandu Jamdade,

Gourishankar B. Swami

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Oct. 24, 2024

Herein, we report the efficient intramolecular dehydrative coupling of symmetrical and unsymmetrical diols for synthesis macrocyclic crown ethers in presence Ni-zeolite as a catalyst under continuous flow module. This method is also macrolactonization seco-acids using or Ru-zeolite. catalysis demonstrated by wide substrate scope with one-time packed to produce 20 polyethers 11 examples broad macrolactones water byproduct.

Language: Английский

Citations

1
Macrocyclic Catalysis Mediated by Water: Opportunities and Challenges DOI
Dejun Zhang, Lingyun Wang, Wanqing Wu

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: unknown

Published: Dec. 2, 2024

This work summarizes macrocyclic catalysis strategies for overcoming aqueous-phase reactivity challenges, product inhibition, and catalyst compatibility in “one-pot” reactions.

Language: Английский

Citations

1
A Quantum-Chemical Study of the Structure of the Complex of Dibenzo-18-Crown-6 Ether with CaCl2 and Its Reactivity in the Oxidation of Ethylbenzene DOI
Ivan Rodionov,

В. И. Анисимова,

Н. В. Улитин

et al.

Polymer Science Series D, Journal Year: 2024, Volume and Issue: 17(4), P. 852 - 857

Published: Dec. 1, 2024

Language: Английский

Citations

0
CrownPhos: A Review of Crown Ether Derivatives Decorated with Phosphorus Donors DOI
Guddekoppa S. Ananthnag

Comments on Inorganic Chemistry, Journal Year: 2023, Volume and Issue: 44(3), P. 161 - 202

Published: Sept. 6, 2023

Crown ethers are cyclic polyethers of varied ring sizes. The ability to bind cations specific size and charge is based on the size, donor atoms present in crown cavity, geometry. host-guest chemistry further enriched by introduction other into cavity. For example, aza-crown wherein one or more oxygen replaced nitrogen donors. replacement appreciably alters cavity host guest molecules. Phosphorus donors can be introduced periphery generate hybrid ligands. In these "CrownPhos" ligand systems, selectively binds hard phosphorus preferentially soft transition metal centers. presence ether alter steric electronic properties thereby modulate catalytic ability. current review focuses various synthetic aspects ethers, thia-crown appended with periphery.

Language: Английский

Citations

0
Enantioselective recognition based on chiral macrocyclic hosts DOI Open Access

Qingyu Zhao,

Rong Fu,

Kang Cai

et al.

Scientia Sinica Chimica, Journal Year: 2023, Volume and Issue: 53(12), P. 2444 - 2459

Published: Sept. 10, 2023

Homochirality is a fundamental structural characteristic of biological systems. Therefore, the recognition and differentiation chiral enantiomers hold significant importance in various fields related to life health. Macrocyclic hosts serve as crucial tools for molecular recognition, construction macrocyclic enantiomeric guests has remained central topic supramolecular chemistry. In recent years, with vibrant development host-guest chemistry, progress been achieved enantioselective based on hosts. This article provides an overview common strategies constructing macrocycles, categorically reviews representative their capabilities, aiming stimulate application outstanding abilities. Finally, current challenges future prospects this field are summarized.

Language: Английский

Citations

0