One-Pot Stereoselective Synthesis of the Naphthofurano-Iminosugars via a [3 + 2] Cycloaddition Reaction DOI

Likai Zhou,

Yaxin Cui,

Xiaoyan Huang

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(18), P. 13235 - 13242

Published: Sept. 10, 2024

This study presents the synthesis of novel naphthofurano-iminosugars (

Language: Английский

Photocatalytic Synthesis of Quinoline-Linked Covalent Organic Frameworks via Three-Component Povarov Reaction DOI
Chengjuan Wu,

Ming‐Zhen Shao,

Jing‐Lan Kan

et al.

ACS Materials Letters, Journal Year: 2024, Volume and Issue: 6(11), P. 5016 - 5022

Published: Oct. 8, 2024

Visible-light-mediated photocatalysis has been widely utilized to produce various organic products due its clean, efficient, and green characteristics. However, examples involving photocatalytic reactions synthesize covalent frameworks (COFs) have rarely reported thus far. Herein, we report for the first time synthesis of a series quinoline-linked COFs with high crystallinity permanent porosity via three-component one-pot Povarov reaction between different aldehydes, amines, phenyl vinyl sulfone. Furthermore, obtained are stable can be employed as efficient photocatalysts promote oxidative hydroxylation arylboronic acids phenols in excellent yields. This polymerization strategy opens new avenue construction facile way.

Language: Английский

Citations

3

Optimizing Enantiomeric Resolution of Chiral Triazoles in Supercritical Fluid Chromatography DOI Open Access
Codruţa Frîncul, Alina Ghinet, Dalila Belei

et al.

Chirality, Journal Year: 2025, Volume and Issue: 37(2)

Published: Jan. 23, 2025

Chirality plays a crucial role in the pharmacological activity of triazoles, key scaffold antifungal agents and various therapeutic applications. This study focuses on optimizing enantiomeric resolution chiral triazoles using supercritical fluid chromatography (SFC) 10 different columns, either immobilized or coated, chlorinated nonchlorinated, cellulose amylose-based stationary phases (CSPs). Four novel two marketed ones (tebuconazole hexaconazole) were separated to determine optimal conditions. The best was achieved CSPs across tested compounds. Optical rotation X-ray crystallography employed absolute configurations purified enantiomers.

Language: Английский

Citations

0

Catalytic Enantioselective Synthesis of Axially Chiral Diaryl Ethers Via Asymmetric Povarov Reaction Enabled Desymmetrization DOI Creative Commons

Zidan Ye,

Wansen Xie,

Wei Liu

et al.

Advanced Science, Journal Year: 2024, Volume and Issue: unknown

Published: July 16, 2024

Axially chiral diaryl ethers represent a distinct class of atropisomers, characterized by unique dual C─O axes system, which have been found in variety natural products, pharmaceuticals, and ligands. However, the catalytic enantioselective synthesis these atropoisomers poses significant challenges, due to difficulty controlling both axes, their more flexible conformations. Herein, an efficient protocol for axially is presented using organocatalyzed asymmetric Povarov reaction-enabled desymmetrization, followed aromatizations. This method yields wide range novel quinoline-based ether good high enantioselectivities. Notably, various aromatization protocols are developed, resulting diverse set polysubstituted quinoline-containing atropisomers. Thermal racemization studies suggested excellent configurational stabilities atropisomers (with barriers up 38.1 kcal mol

Language: Английский

Citations

3

Efficient one-pot synthesis of the unexpected fused multicyclic iminosugars by an aza-Diels–Alder mechanism DOI
Jilai Wu,

Lulu Su,

Tongguan Jia

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(23), P. 6530 - 6534

Published: Jan. 1, 2022

A simple and efficient one-pot protocol has been developed by an aza-Diels–Alder mechanism for the stereoselective synthesis of novel fused multicyclic iminosugars with structural diversity.

Language: Английский

Citations

11

Highly Enantioselective Three-Component Povarov Reaction for Direct Construction of Azaspirocycles DOI

Nan-Fang Mo,

Ying Zhang, Zheng‐Hui Guan

et al.

Organic Letters, Journal Year: 2022, Volume and Issue: 24(35), P. 6397 - 6401

Published: Aug. 26, 2022

An asymmetric organocatalyzed three-component Povarov reaction to construct azaspirocycles has been developed. A chiral phosphoric acid OCF-CPA bearing o-CF3-aryl on the H8–BINOL-framework is highly efficient in reaction. The was carried out under mind conditions for synthesis of a range high yields and excellent enantioselectivities, thus expending substrate scope traditional

Language: Английский

Citations

10

One‐Pot Stereoselective Synthesis of Different Fused Multicyclic Iminosugars Based on the Iminium‐Ion Intermediate DOI

Song Xie,

Jilai Wu,

Likai Zhou

et al.

Chinese Journal of Chemistry, Journal Year: 2023, Volume and Issue: 42(2), P. 142 - 150

Published: Sept. 15, 2023

Comprehensive Summary Different novel fused multicyclic iminosugars were synthesized from D‐ribose tosylate, aniline and vinyl ethyl ether by one‐pot three‐component stereoselective [4+2] reaction at different temperatures. The iminium‐ion is the key intermediate for reaction. As a result, several complex 3a obtained aza‐Diels‐Alder mechanism 60 °C, while series of aza‐ C ‐glycosides 5a prepared Mannich room temperature accompanied another tetrahydroquinoline‐fused 4a (tricyclic derivatives) through cycloaddition. This strategy will help to construct structurally diverse bioactive iminosugar analogues.

Language: Английский

Citations

6

Organocatalytic regio- and enantioselective formal [4+2]-annulation of chiral nitrogen-containing dipoles DOI Open Access
Tao Wang,

Boming Shen,

Xuling Chen

et al.

Chemical Synthesis, Journal Year: 2023, Volume and Issue: 3(2), P. 9 - 9

Published: Jan. 1, 2023

Quinidine-catalyzed regio- and enantioselective formal [4 + 2]-cycloadditions of 2-(4H-benzo[d][1,3]oxazin-4-yl)acrylates with N-tosyl-2-methylenebut-3-enoates 2-methylene-3-oxoalkanoates have been developed for the first time. The reaction features in situ formation chiral nitrogen-containing dipolar intermediates, a ring-opening/Michael addition/annulation cascade works well over broad substrate scope to furnish tetrahydroquinolines high yields asymmetric induction under mild conditions.

Language: Английский

Citations

5

One-Pot Stereoselective Synthesis of Furantetrahydroquinoline Derivatives Using d/l-Ribose with a 2,3-O-Isopropylidene Group DOI
Jilai Wu,

Song Xie,

Likai Zhou

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(17), P. 12445 - 12450

Published: Aug. 18, 2023

An efficient and convenient strategy has been successfully developed for the preparation of novel furantetrahydroquinoline derivatives using d/l-ribose with a 2,3-O-isopropylidene group through aza-Diels-Alder mechanism. This method high atom step economy, stereoselectivity, gram-scale synthesis (yield 67%).

Language: Английский

Citations

5

Enantioselective synthesis of pyrroloquinolines via a three-component Povarov reaction with aminoindoles DOI

Zijie Zhou,

Ling Ye, Yang Lu

et al.

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 10(24), P. 6219 - 6224

Published: Jan. 1, 2023

This protocol provides concise access to enantioenriched pyrroloquinolines, and presents an alternative methodology for functionalizing the carbocyclic ring of indoles.

Language: Английский

Citations

4

Multicomponent double Povarov reaction for julolidine: Synthesis and mechanistic insights DOI
Sandra Milena Bonilla Castañeda, Walysson Ferreira de Paiva, Gabriel Abranches Dias Castro

et al.

Molecular Catalysis, Journal Year: 2024, Volume and Issue: 568, P. 114487 - 114487

Published: Aug. 29, 2024

Language: Английский

Citations

1