Photoredox Catalytic Deracemization Enabled Enantioselective and Modular Access to Axially Chiral N‐Arylquinazolinones DOI
Yilin Liu,

Mengqi Chu,

Xiangtao Li

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown

Published: July 24, 2024

Visible light-driven photocatalytic deracemization is highly esteemed as an ideal tool for organic synthesis due to its exceptional atom economy and synthetic efficiency. Consequently, successful instances of allenes have been established, where the activated energy photosensitizer should surpass that substrates, representing intrinsic requirement. Accordingly, this method not applicable axially chiral molecules with significantly high triplet energies. In study, we present a photoredox catalytic approach enables efficient valuable yet challenging-to-access 2-azaarene-functionalized quinazolinones. The substrate scope extensive, allowing both 3-axis unmet 1-axis assembly through facile oxidation diverse central 2,3-dihydroquinazolin-4(1H)-ones can be easily prepared achieve enantiomer enrichment via deracemization. Mechanistic studies reveal importance selection in attaining excellent chemoselectivity highlight indispensability Brønsted acid enabling enantioselective protonation accomplish

Language: Английский

Chiral phosphoric acid-catalyzed dual-ring formation for enantioselective construction of N–N axially chiral 3,3′-bisquinazolinones DOI

Liang-Yuan Pu,

Yujiao Zhang, Wei Liu

et al.

Chemical Communications, Journal Year: 2022, Volume and Issue: 58(94), P. 13131 - 13134

Published: Jan. 1, 2022

In contrast with the well-developed C-C and C-N axial chirality, research focusing on catalytically asymmetric synthesis of N-N axially chiral compounds is still limited. As a privileged subunit many antibiotics, 3,3'-bisquinazolinones has not been updated atroposelective construction. Herein, we firstly report phosphoric acid-catalyzed dual-ring formation strategy leading to aforementioned good chemical yields enantioselectivities. Notably, metal-free reaction conditions are another advantage this procedure.

Language: Английский

Citations

27
Asymmetric organocatalytic (3 + 2) annulation of propargylic alcohols with indolylnaphthalenols: synergistic construction of axial and central chirality DOI
Yan Xia,

Meiwen Liu,

Chenxiao Qian

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 10(1), P. 30 - 34

Published: Nov. 14, 2022

Organocatalytic enantioselective construction of chiral spiro N , -acetal carbon stereocenters and axially 3-arylindoles has been achieved in one pot.

Language: Английский

Citations

26
Synthesis of C—N Axial Chirality N‐Arylindoles via Pd(II)‐Catalyzed Free Amine‐Directed Atroposelective C—H Olefination† DOI
Lei Wang, Wen‐Kui Yuan, Zhen‐Kai Wang

et al.

Chinese Journal of Chemistry, Journal Year: 2023, Volume and Issue: 41(21), P. 2788 - 2792

Published: July 3, 2023

Comprehensive Summary Axially chiral N ‐arylindoles bearing a stereogenic C—N axis are unique important scaffolds in natural products, advance materials, pharmaceuticals and privileged ligands or catalysts. Herein, we report the direct synthesis of axially through Pd‐catalyzed free amine‐directed atroposelective C—H olefination enabled by spiro phosphoric acid (SPA) ligand. A wide range enantioenriched ‐aromatic amine indoles were obtained high yields with good enantioselectivities (35 examples, up to 91% yield 96% ee). The products group offer an effective functional handle for down‐stream diversity‐oriented synthesis.

Language: Английский

Citations

14
Advances in Catalytic Asymmetric Reactions Involving o-Hydroxyphenyl Substituted p-Quinone Methides★ DOI Open Access
Shuang Yang,

Ningyi Wang,

Qingqing Hang

et al.

Acta Chimica Sinica, Journal Year: 2023, Volume and Issue: 81(7), P. 793 - 793

Published: Jan. 1, 2023

o-Hydroxyphenyl substituted p-quinone methides (p-QMs) belong to a class of p-QMs with unique advantages.They not only maintain the high reactivity p-QMs, but also have more reactive and activation sites owing introduction hydroxyl group.Therefore, o-hydroxyphenyl wide applications in synthetic medicinal chemistry.The catalytic asymmetric 1,6-conjugate addition [4＋n] cycloaddition developed very rapidly recent years, which become efficient strategies for synthesis chiral oxygen-containing heterocycles arylmethanes potential bioactivity.This review summarizes reactions involving points out remaining challenges this research area, will open new window design type their involved reactions.

Language: Английский

Citations

13
Photoredox Catalytic Deracemization Enabled Enantioselective and Modular Access to Axially Chiral N‐Arylquinazolinones DOI
Yilin Liu,

Mengqi Chu,

Xiangtao Li

et al.

Angewandte Chemie International Edition, Journal Year: 2024, Volume and Issue: unknown

Published: July 24, 2024

Visible light-driven photocatalytic deracemization is highly esteemed as an ideal tool for organic synthesis due to its exceptional atom economy and synthetic efficiency. Consequently, successful instances of allenes have been established, where the activated energy photosensitizer should surpass that substrates, representing intrinsic requirement. Accordingly, this method not applicable axially chiral molecules with significantly high triplet energies. In study, we present a photoredox catalytic approach enables efficient valuable yet challenging-to-access 2-azaarene-functionalized quinazolinones. The substrate scope extensive, allowing both 3-axis unmet 1-axis assembly through facile oxidation diverse central 2,3-dihydroquinazolin-4(1H)-ones can be easily prepared achieve enantiomer enrichment via deracemization. Mechanistic studies reveal importance selection in attaining excellent chemoselectivity highlight indispensability Brønsted acid enabling enantioselective protonation accomplish

Language: Английский

Citations

5