Construction of Sulfur(IV)‐Chiral Six‐Membered Heterocycles by Pd‐Catalyzed Asymmetric (4+2) Dipolar Cyclization DOI

Fen‐Ya Xiong,

Sudip Pan,

Bao‐Cheng Wang

et al.

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

Published: Nov. 27, 2024

Abstract Chiral sulfur‐containing compounds play an important role in asymmetric catalysis and synthesis, chiral pharmaceuticals, materials. While great progress has been made the synthesis of these compounds, catalytic heterocycles remains relatively limited compared to acyclic ones. In this study, we successfully report efficient highly selective structurally diverse chirality‐at‐sulfur(IV) six‐membered under mild conditions via a Pd‐catalyzed (4+2) dipolar cyclization. More importantly, products enable enantioselective preparation variety other S‐stereogenic derivatives.

Language: Английский

Palladium-Catalyzed Decarboxylative Allylic Sulfonylation of Vinyloxazolidine-2,4-diones: Synthesis of γ-Sulfonyl-α,β-unsaturated Amides DOI
Wei‐Cheng Yuan, Xiaohui Fu, Yanping Zhang

et al.

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

Published: Feb. 10, 2025

A palladium-catalyzed decarboxylative allylic sulfonylation reaction of vinyloxazolidine-2,4-diones with inexpensive and readily available sodium sulfinates as reagents has been developed. Under the catalysis Pd(PPh3)4, a wide range γ-sulfonyl-α,β-unsaturated amides can be synthesized in good to excellent yields. The developed protocol is characterized by exclusive regioselectivity, mild conditions, broad substrate scope, functional group tolerance, suitable for gram-scale synthesis.

Language: Английский

Citations

0
Nanofibrous membrane for red fluorescent probe of palladium: Applications in environmental analysis and cells imaging DOI
Mengting Wang, Yue-Yue Zhao, Han Zhang

et al.

Microchemical Journal, Journal Year: 2025, Volume and Issue: 213, P. 113748 - 113748

Published: April 23, 2025

Language: Английский

Citations

0
Diastereoselective Double Annulation of Allenoates with Povarov Adducts: Modular Synthesis of Multisubstituted Pyrroloquinolines DOI
Srinivasarao Yaragorla,

Doma Arun

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(22), P. 16838 - 16849

Published: Nov. 6, 2024

Herein, we report an atom-economical, one-pot, four-component, diastereoselective double-annulation reaction to construct polyfused pyrroloquinolines. This highlights the cyclization of in situ

Language: Английский

Citations

2
Asymmetric Construction of Chiral 2‐Azetines and Axially Chiral Tetrasubstituted Allenes via Phosphine Catalysis DOI Open Access
Yi Tang, Mingxia Huang,

Jingrong Jin

et al.

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

Published: Nov. 11, 2024

Chiral 2-azetines and allenes are highly valuable structural units in natural products useful chemicals. However, enantioselective synthesis of both has been extremely challenging. Herein, we present asymmetric construction chiral (70-98 % yields up to 96 ee) through phosphine-catalyzed [2+2] annulation yne-enones with sulfamate-derived cyclic imines. These were easily transformed into upon treatment Et

Language: Английский

Citations

1
Ni-Catalyzed Asymmetric Decarboxylation for the Construction of Carbocycles with Contiguous Quaternary Carbon Stereocenters DOI Creative Commons

Yicheng He,

Biwei Yan,

Cheng Ma

et al.

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

Published: Nov. 26, 2024

The first Ni-catalyzed asymmetric decarboxylative strategy for the construction of carbocycles with contiguous quaternary all-carbon stereocenters is reported. key to success these reactions utilization rationally designed allenylic methylene cyclic carbonates as substrates Ni catalysis. floppy group exerts unique electronic properties on carbonate, which allows further nucleophilic annulations alkenes. These can be performed at room temperature and feature wide functional tolerance excellent induction that typically >94% ee. mechanistic insights imply this conceptually new chemistry completely different from previous reports catalytic transformation carbonates, thus, it offers an inventive novel methodology create complex enantio-enriched molecules.

Language: Английский

Citations

1
Pd-Catalyzed Sequential Intramolecular Annulation/ Intermolecular [3+2] Cycloaddition of 5-Allenyloxazolidine-2,4-diones with Dipoles: Synthesis of Spiroheterocycles DOI
Yujie Dong, Jun Liu,

Rongjin Ning

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(76), P. 10516 - 10519

Published: Jan. 1, 2024

Pd-catalyzed sequential intramolecular annulation/intermolecular [3+2] cycloaddition of 5-allenyloxazolidine-2,4-diones with dipoles was achieved. Under palladium catalysis, various reacted 1,3-dipoles such as nitrile

Language: Английский

Citations

0
Palladium-Catalyzed [3+2] Cycloaddition of 4-Vinyl-4-Butyro-lactones with Sulfamate-Derived Cyclic Imines: Construction of Sulfamate-Fused Pyrrolidines DOI
Honghao Sun,

Siyuan Ding,

Bo Wang

et al.

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: unknown

Published: Jan. 1, 2024

The palladium-catalyzed [3 + 2] decarboxylative cycloaddition of 4-vinyl-4-butyrolactones with sulfamate-derived cyclic imines has been developed, providing the sulfamate-fused pyrrolidine derivatives in high yields good diastereoselectivities.

Language: Английский

Citations

0
Asymmetric Construction of Chiral 2‐Azetines and Axially Chiral Tetrasubstituted Allenes via Phosphine Catalysis DOI Open Access
Yi Tang, Mingxia Huang,

Jingrong Jin

et al.

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

Published: Nov. 11, 2024

Abstract Chiral 2‐azetines and allenes are highly valuable structural units in natural products useful chemicals. However, enantioselective synthesis of both has been extremely challenging. Herein, we present asymmetric construction chiral (70–98 % yields up to 96 ee) through phosphine‐catalyzed [2+2] annulation yne‐enones with sulfamate‐derived cyclic imines. These were easily transformed into upon treatment Et 3 SiH, BF ⋅ 2 O water at rt for minutes. Based on the above transformations, a concise one‐pot synthetic procedure combining imines under phosphine catalysis sequential reduction/isomerization/ring‐opening reaction was thus set up, providing axially tetrasubstituted satisfactory enantioselectivities (56–90 91 ee).

Language: Английский

Citations

0
Synthesis of allenones via nickel-catalyzed reductive coupling of propargyl esters with acyl chlorides DOI Creative Commons
Zhen Song, Yueming Wang, Ming Ma

et al.

Tetrahedron Chem, Journal Year: 2024, Volume and Issue: unknown, P. 100113 - 100113

Published: Nov. 1, 2024

Language: Английский

Citations

0
Construction of Sulfur(IV)‐Chiral Six‐Membered Heterocycles by Pd‐Catalyzed Asymmetric (4+2) Dipolar Cyclization DOI

Fen‐Ya Xiong,

Sudip Pan,

Bao‐Cheng Wang

et al.

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

Published: Nov. 27, 2024

Abstract Chiral sulfur‐containing compounds play an important role in asymmetric catalysis and synthesis, chiral pharmaceuticals, materials. While great progress has been made the synthesis of these compounds, catalytic heterocycles remains relatively limited compared to acyclic ones. In this study, we successfully report efficient highly selective structurally diverse chirality‐at‐sulfur(IV) six‐membered under mild conditions via a Pd‐catalyzed (4+2) dipolar cyclization. More importantly, products enable enantioselective preparation variety other S‐stereogenic derivatives.

Language: Английский

Citations

0