Catalytic and Stereoselective Transformations with Easily Accessible and Purchasable Allyl and Alkenyl Fluorides DOI
Paulo H. S. Paioti, Stella A. Gonsales, Shibo Xu

et al.

Angewandte Chemie, Journal Year: 2022, Volume and Issue: 134(46)

Published: Aug. 26, 2022

Abstract Stereochemically defined organofluorine compounds are vital to drug discovery and many applicable catalytic strategies have been introduced for accessing these entities stereoselectively. One approach entails incorporation of a fluorine atom (C−F bond formation) or an moiety (e.g., CF 3 2 H), another exploits commercially available with one more atoms. Here, we present the state‐of‐the‐art regarding use alkenyl allylic fluorides in preparation stereochemically fluoro‐organic molecules. Allylic may be purchased generated from acid, carboxylate salt, ester, aldehyde hydrate, ketone bearing several atoms next carbonyl group. We underscore untapped potential purchasable compounds, fluorides, as launching points development stereoselective processes that value therapeutic science.

Language: Английский

Recent advances in the applications of pyrazolone derivatives in enantioselective synthesis DOI
Xiaoze Bao, Xingyue Wang,

Jin‐Miao Tian

et al.

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(12), P. 2370 - 2386

Published: Jan. 1, 2022

Pyrazolones and pyrazoles, featuring nitrogen-nitrogen bonds, are two of the most important classes heterocycles, owing to their widespread occurrence in medicinal chemistry functional materials. The last decade has witnessed a rapid increase construction chiral pyrazolone pyrazole derivatives, with application derivatives as powerful synthons. Since our review 2018, large number new achievements emerged this area, requiring timely update. Thus, summarizes these elegant based on multiple reactive sites different In addition, mechanisms interesting biological investigations relating corresponding products also discussed.

Language: Английский

Citations

41

Pd-Catalysed asymmetric allylic alkylation of heterocycles: a user's guide DOI
F. Richard,

Paul G. Clark,

Al Hannam

et al.

Chemical Society Reviews, Journal Year: 2024, Volume and Issue: 53(4), P. 1936 - 1983

Published: Jan. 1, 2024

This review analyses recent advances and strategies employed in the Pd-AAA of nucleophilic prochiral heterocycles. Each section is focused on a specific heterocycle, where optimisation data reaction scope have been carefully analysed.

Language: Английский

Citations

11

Catalytic and Stereoselective Transformations with Easily Accessible and Purchasable Allyl and Alkenyl Fluorides DOI
Paulo H. S. Paioti, Stella A. Gonsales, Shibo Xu

et al.

Angewandte Chemie International Edition, Journal Year: 2022, Volume and Issue: 61(46)

Published: Aug. 26, 2022

Stereochemically defined organofluorine compounds are vital to drug discovery and many applicable catalytic strategies have been introduced for accessing these entities stereoselectively. One approach entails incorporation of a fluorine atom (C-F bond formation) or an moiety (e.g., CF3 CF2 H), another exploits commercially available with one more atoms. Here, we present the state-of-the-art regarding use alkenyl allylic fluorides in preparation stereochemically fluoro-organic molecules. Allylic may be purchased generated from acid, carboxylate salt, ester, aldehyde hydrate, ketone bearing several atoms next carbonyl group. We underscore untapped potential purchasable compounds, fluorides, as launching points development stereoselective processes that value therapeutic science.

Language: Английский

Citations

24

Discovery of novel NSAID hybrids as cPLA2/COX-2 dual inhibitors alleviating rheumatoid arthritis via inhibiting p38 MAPK pathway DOI
Nan Cai, Xiang Gao, Yang Li

et al.

European Journal of Medicinal Chemistry, Journal Year: 2024, Volume and Issue: 267, P. 116176 - 116176

Published: Jan. 24, 2024

Language: Английский

Citations

4

Pd-Catalyzed Asymmetric Synthesis of Chiral 2-Trifluoromethyl-4-(indol-3-yl)-4H-chromene Derivatives DOI

Bangzhong Wang,

Luyang Sun, Pengyue Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 29, 2025

This paper presents a new strategy for the construction of chiral 4H-chromene skeleton. A series 2-trifluoromethyl-4-(indol-3-yl)-4H-chromenes were synthesized in moderate to good yields (60-92%) with excellent enantioselectivity (up 97% ee) through palladium-catalyzed asymmetric condensation 2H-chromenes and indoles. These trifluoromethylated, stereochemically rich building blocks hold potential value medicinal chemistry.

Language: Английский

Citations

0

Pd-Catalyzed Asymmetric Etherification of 2H-chromenes: Enantioselective Construction of Chiral 4-Alkoxy-4H-chromenes DOI

Bangzhong Wang,

Luyang Sun, Pengyue Zhang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A new strategy for the construction of a chiral 4-alkoxy-4 H -chromene skeleton was reported. series -chromenes containing trifluoromethyl group were obtained in good yields and excellent enantioselectivity.

Language: Английский

Citations

0

Diastereoselective Formal [3+3] Cascade Cyclization towards Fused 4‐Fluoroalkylated 3,4‐Dihydro‐2H‐pyrans via Copper Catalysis DOI

Weigao Hu,

Jiawen Yin,

Zhiyong Li

et al.

Chinese Journal of Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: April 25, 2025

Comprehensive Summary The cycloaddition and annulation reactions offer a powerful method toward various important substituted 3,4‐dihydro‐2 H ‐pyran architectures. Nevertheless, the transformation for preparing fused‐polycyclic ones still remains challenging yet highly desirable until now. Herein, we report novel formal [3+3] cascade cyclization reaction to provide lactam‐fused 4‐fluoroalkylated 3,4‐dihydropyran skeletons bearing three contiguous tertiary carbon centers via copper catalysis. Of note, these annulations proceeded in an exclusively diastereoselective manner through successive inert C(sp 2 )‐Cl 3 )‐H functionalization, which exhibited site‐selectivity stereoselectivity. Additionally, evaluations on biological activities of obtained products revealed that several display inhibitory activity against Siha H1975 cancer cell lines.

Language: Английский

Citations

0

Novel trifluoromethyl ketone derivatives as oral cPLA2/COX-2 dual inhibitors for resolution of inflammation in rheumatoid arthritis DOI
Nan Cai, Xiang Gao, Wenjing Li

et al.

Bioorganic Chemistry, Journal Year: 2024, Volume and Issue: 148, P. 107453 - 107453

Published: May 14, 2024

Language: Английский

Citations

2

Diastereospecific Enantiodivergent Allylation of Pyrazolones as an Entry to β‐Aminoamides DOI Creative Commons

Nick Wannenmacher,

Martin Heberle,

Xin Yu

et al.

Advanced Synthesis & Catalysis, Journal Year: 2022, Volume and Issue: 364(19), P. 3396 - 3403

Published: April 7, 2022

Abstract A diastereospecific enantiodivergent allylation of pyrazolones is reported which catalyzed by a planar chiral pentaphenylferrocene based palladacycle. With the same catalyst batch both product enantiomers were selectively available. The method applicable to structurally diverse substrates and gave products with enantiomeric excesses between 85 94%. In addition, we could show that are transformable into β‐aminoamides. magnified image

Language: Английский

Citations

11

Palladium‐Catalyzed Asymmetric Trifluoromethylated Allylic Alkylation of N‐Substituted Glycine Ethyl Esters with α‐(Trifluoromethyl)alkenyl Acetates DOI

Shuaibo Zhang,

Dong Li,

Bangzhong Wang

et al.

European Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 26(36)

Published: July 19, 2023

Abstract An efficient strategy for asymmetric trifluoromethylated allylic alkylation of easily available N ‐substituted glycine ethyl esters with α ‐(trifluoromethyl)alkenyl acetates has been developed. Catalyzed by a [Pd(C 3 H 5 )Cl] 2 /( R )‐BINAP, various trifluoromethyl‐containing ester derivatives are afforded good yields and excellent enantioselectivities. The product can be readily converted into diverse fluoro‐substituted species, which shows the practicability this method.

Language: Английский

Citations

6