Catalytic Enantioselective Synthesis of Inherently Chiral Calix[4]arenes via Sequential Povarov Reaction and Aromatizations DOI

Shaoze Yu,

Mengyao Yuan,

Wansen Xie

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(45)

Published: July 8, 2024

Abstract Inherently chiral calix[4]arenes represent a unique type of molecules with significant applications, yet their catalytic enantioselective synthesis remains largely underexplored. We report herein the inherently through sequential organocatalyzed Povarov reaction and aromatizations. The phosphoric acid catalyzed three‐component involving amino group‐substituted calix[4]arenes, aldehydes (di)enamides desymmetrized prochiral calix[4]arene substrates, which was followed by various aromatization methods, resulting in diverse array novel quinoline‐containing good yields high enantioselectivities (up to 75 % yield, 99 ee). large‐scale derivatizations products highlight value this method. Furthermore, preliminary exploration into photophysical chiroptical properties demonstrate potential applications these molecules.

Language: Английский

Catalytic Enantioselective Synthesis of Inherently Chiral Calix[4]arenes via Sequential Povarov Reaction and Aromatizations DOI

Shaoze Yu,

Mengyao Yuan,

Wansen Xie

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: 63(45)

Published: July 8, 2024

Inherently chiral calix[4]arenes represent a unique type of molecules with significant applications, yet their catalytic enantioselective synthesis remains largely underexplored. We report herein the inherently through sequential organocatalyzed Povarov reaction and aromatizations. The phosphoric acid catalyzed three-component involving amino group-substituted calix[4]arenes, aldehydes (di)enamides desymmetrized prochiral calix[4]arene substrates, which was followed by various aromatization methods, resulting in diverse array novel quinoline-containing good yields high enantioselectivities (up to 75 % yield, 99 ee). large-scale derivatizations products highlight value this method. Furthermore, preliminary exploration into photophysical chiroptical properties demonstrate potential applications these molecules.

Language: Английский

Citations

9
Catalytic Atroposelective Construction of Diarylethers and Diarylamines DOI

Rehmatullah Farooqi,

Aleena Mustafai,

Alemayehu Gashaw Woldegiorgis

et al.

ACS Catalysis, Journal Year: 2025, Volume and Issue: unknown, P. 7891 - 7911

Published: April 29, 2025

Language: Английский

Citations

0
Pyridinylphenols: advances in multidisciplinary research and applications driven by multifunctional properties DOI

Zhen-Fu Lin,

Zhongyu Li, Jie Li

et al.

Dyes and Pigments, Journal Year: 2025, Volume and Issue: unknown, P. 112866 - 112866

Published: May 1, 2025

Language: Английский

Citations

0
Catalytic kinetic resolution of helical polycyclic phenols via an organocatalyzed enantioselective dearomative amination reaction DOI Creative Commons

Anqi Chu,

Boyan Zhu, Xiaoyong Zhang

et al.

Science Advances, Journal Year: 2024, Volume and Issue: 10(47)

Published: Nov. 22, 2024

Despite the considerable potential applications for helically chiral molecules across various sectors, their catalytic asymmetric synthesis remains nascent and has seen very limited advancement compared to that of central axial compounds, primarily owing scarcity available starting materials immense challenges associated with achieving stereochemical control. Herein, we report an innovative approach facile kinetic resolution uniquely structured stereochemically complex helical polycyclic phenols by using a steric hindrance–regulated enantioselective dearomative amination reaction. The distinguished aspects this method include exceptional stability dearomatized products impressive versatility recovered substrates in construction enantioenriched frameworks. This work showcases strategic incorporation appropriate groups near reaction site electron-rich aromatic compound can indeed enable interrupted Friedel-Crafts reaction, thus opening alternate avenue study dearomatization nonfunctionalized arenes.

Language: Английский

Citations

2
Asymmetric Synthesis of Helicenes from Centrally Chiral Precursors DOI
Hui Yang,

Hong‐Xia Feng,

Ling Zhou

et al.

European Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 27(41)

Published: July 19, 2024

Abstract Chiral helicenes are widely used in fields related to organic materials and molecular machines relevant molecules, as well serving privileged frameworks for chiral ligands catalysts. Therefore, the research into asymmetric routes synthesis of helical compounds has garnered significant interest recent years. In this regard, chirality conversion/transfer from precursors emerged a powerful strategy construction helicenes, allowing various types compounds. This become will remain prominent topic field synthesis. review article, described between 2012 2024, approaches by conversion or transfer centrally summarized.

Language: Английский

Citations

1
Enantioselective Synthesis of Helically Chiral Molecules Enabled by Asymmetric Organocatalysis DOI
Qingqin Huang, Yuping Tang,

Cong-Zhen Zhang

et al.

ACS Catalysis, Journal Year: 2024, Volume and Issue: 14(21), P. 16256 - 16265

Published: Oct. 19, 2024

Helical systems have attracted considerable interest across multiple scientific fields due to not only their essential roles in biological processes but also potential unveil chirality-associated phenomena, properties, and functionalities. Today, the distinctive topologies of helicenes found extensive applications materials science, molecular recognition, asymmetric catalysis owing structural diversity unique optical electronic characteristics. Nonetheless, contrast advancements synthesis optically pure point-chiral axially chiral compounds, catalytic enantioselective assembly helically molecules remains its nascent stages. This Perspective delves into latest developments organocatalytic emphasizing both strengths limitations existing literature, with perspectives on remaining challenges within field. It is expected that this will serve as a catalyst for innovation, inspiring creation more efficient strategies synthesize molecules.

Language: Английский

Citations

1
Catalytic Enantioselective Synthesis of Inherently Chiral Calix[4]arenes via Sequential Povarov Reaction and Aromatizations DOI

Shaoze Yu,

Mengyao Yuan,

Wansen Xie

et al.

Angewandte Chemie, Journal Year: 2024, Volume and Issue: 136(45)

Published: July 8, 2024

Abstract Inherently chiral calix[4]arenes represent a unique type of molecules with significant applications, yet their catalytic enantioselective synthesis remains largely underexplored. We report herein the inherently through sequential organocatalyzed Povarov reaction and aromatizations. The phosphoric acid catalyzed three‐component involving amino group‐substituted calix[4]arenes, aldehydes (di)enamides desymmetrized prochiral calix[4]arene substrates, which was followed by various aromatization methods, resulting in diverse array novel quinoline‐containing good yields high enantioselectivities (up to 75 % yield, 99 ee). large‐scale derivatizations products highlight value this method. Furthermore, preliminary exploration into photophysical chiroptical properties demonstrate potential applications these molecules.

Language: Английский

Citations

0