Cited by Synthesis of <i>N</i>-Heteroaryl <i>C</i>-Glycosides and Polyhydroxylated Alkanes with Diaryl Groups from Unprotected Sugars

Solvent-Controlled Enantioselective Allylic C–H Alkylation of 2,5-Dihydrofuran via Synergistic Palladium/Nickel Catalysis DOI

Fule Wu,

Hongkai Wang,

Zhenwei Wu

et al.

Journal of the American Chemical Society, Journal Year: 2025, Volume and Issue: unknown

Published: May 1, 2025

Enantioenriched, substituted tetrahydrofuran skeletons extensively occur in natural products, bioactive targets, and organic frameworks. The rapid diverse synthesis of these molecules is highly desired yet challenging. Herein, we present a practical synthetic strategy for asymmetric allylic C-H bond functionalization oxyheterocyclic alkenes by making use the synergistic catalysis achiral Pd complex chiral N,N'-dioxide-Ni(II) catalyst. Notably, chemodivergent alkylated products hydroalkylated was readily achieved good outcomes via regulation solvents. Furthermore, post-transformation functionalized 2,5-dihydrofurans provides an innovative route to access skeleton compounds containing multiple stereocenters.

Language: Английский

Citations

Diversification of Glycosyl Compounds via Glycosyl Radicals DOI

Yi Jiang, Yijun Zhang,

Boon Chong Lee

et al.

Angewandte Chemie, Journal Year: 2023, Volume and Issue: 135(38)

Published: June 7, 2023

Abstract Glycosyl radical functionalization is one of the central topics in synthetic carbohydrate chemistry. Recent advances metal‐catalyzed cross‐coupling chemistry and metallaphotoredox catalysis provided powerful platforms for glycosyl diversification. In particular, discovery new precursors conjunction with these advanced reaction technologies have significantly expanded space compound synthesis. this Review, we highlight most recent progress area starting from 2021, reports included will be categorized based on different types better clarity.

Language: Английский

Citations

Regio- and Enantioselective Hydromethylation of 3-Pyrrolines and Glycals Enabled by Cobalt Catalysis DOI

Mengyang Shen,

C. NIU,

Xuchao Wang

et al.

JACS Au, Journal Year: 2024, Volume and Issue: 4(6), P. 2312 - 2322

Published: June 11, 2024

Enantioenriched 3-methylpyrrolidine, with its unique chiral nitrogen-containing core skeleton, exists widely in various functional molecules, including natural products, bioactive compounds, and pharmaceuticals. Traditional methods for synthesizing these valuable methyl-substituted heterocycles often involve enzymatic processes or complex procedures auxiliaries, limiting the substrate scope efficiency. Efficient catalytic methylation, especially an enantioselective manner, has been a long-standing challenge chemical synthesis. Herein, we present novel approach remote stereoselective installation of methyl group onto N-heterocycles, leveraging CoH-catalyzed asymmetric hydromethylation strategy. By effectively combining commercial cobalt precursor modified bisoxazoline (BOX) ligand, variety easily accessible 3-pyrrolines can be converted to enantiopure 3-(isotopic labeling)methylpyrrolidine compounds outstanding enantioselectivity. This efficient protocol streamlines two-step synthesis enantioenriched which previously required up five six steps under harsh conditions expensive starting materials.

Language: Английский

Citations

Synthesis of C-Alkyl Glycosides from Alkyl Bromides and Glycosyl Carboxylic Acids via Ni/Photoredox Dual Catalysis DOI

Wei‐Yu Shi,

Jiajun Ma,

Hu-Yi Li

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(16), P. 11136 - 11147

Published: Aug. 6, 2024

-Alkyl glycosides, an important class of C-glycosides, are widely found in various drugs and natural products. The synthesis

Language: Английский

Citations

Application of Redox-Active Ester Catalysis to the Synthesis of Pyranose Alkyl C-Glycosides DOI

Joseph R. Romeo,

Jon D. Lucera,

Drew Jensen

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(20), P. 3760 - 3765

Published: May 12, 2023

The direct coupling of shelf-stable, tetrachloro-N-hydroxyphthalimide ester (TCNHPI) glycosyl donors with a variety alkylzinc reagents under redox catalysis is described. Alkyl C-glycosides are formed directly by decarboxylative, Negishi-type process in 31-73% yields without the need for photocatalytic activation or additional reductants. Extension this approach to TCNHPI stereodefined α-alkoxy furan-containing halides enabled de novo synthesis methylene-linked exo-C-disaccharides via an Achmatowicz rearrangement.

Language: Английский

Citations

Recent Advance in the β‐Stereoselective Synthesis of 2‐Deoxy Glycosides DOI

Qiang Zhang, Hai Dong

Asian Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 13(8)

Published: May 31, 2024

Abstract Compounds containing a 2‐deoxy β ‐glycoside linkage play important roles in carbohydrate chemistry, serving as potential therapies with significant biological properties. From the viewpoint of synthesis, many strategies developed recent years targeted stereoselective construction glycosides. This review aims to summarise advances synthetic routes toward β‐ glycosides over last decade. Where associated, practical applications these total synthesis natural products are highlighted.

Language: Английский

Citations

Cobalt’s Dual Role in Promoting C3-Glycosylation of Indoles: Unraveling Mechanistic Insights DOI

Qiu-Qi Mu,

Aoxin Guo, Xin Cai

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(38), P. 7040 - 7045

Published: Sept. 18, 2023

In this study, we present a cobalt-catalyzed C3-glycosylation of indoles using unfunctionalized glycals, yielding 3-indolyl-C-deoxyglycosides. These compounds hold promise as sodium-dependent glucose cotransporter 2 (SGLT2) inhibitors for treating type diabetes. Control experiments unveiled that cobalt assumes dual role, facilitating catalytic C-glycosylation while unexpectedly driving the anomerization α-anomers through endocyclic cleavage C1-O5 bond, resulting in formation β-C-deoxyglycosides. Furthermore, density functional theory (DFT) calculations shed light on reaction mechanism, emphasizing significant role pyridine group indole stabilizing transition states and intermediates.

Language: Английский

Citations

Transition-metal-catalyzed asymmetric functionalization of simple heterocycles: Facile access to chiral saturated heterocycles DOI

Chun Liu,

Xin Kui,

Qiyuan Lu

et al.

Chem Catalysis, Journal Year: 2023, Volume and Issue: 4(1), P. 100798 - 100798

Published: Nov. 7, 2023

Language: Английский

Citations

Synthesis of C-glycosides enabled by palladium-catalyzed glycosylation reactions DOI

Wenli Tong,

Jie‐Ping Wan, Jianchao Liu

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(23), P. 6918 - 6941

Published: Jan. 1, 2024

This review highlights the recent progress in palladium-catalyzed C -glycosylation reactions for synthesis of -glycosides.

Language: Английский

Citations

Highly Regio-/Stereoselective Synthesis of Carbohydrates with Unsaturated Glycosyl Donors under Mild Conditions DOI

Nengzhong Wang, Nianyu Huang, Hui Yao

et al.

Synlett, Journal Year: 2024, Volume and Issue: unknown

Published: June 19, 2024

Abstract Carbohydrates and their conjugates play important roles in life activities drug development. Our group was committed to the general effective glycosylation methods application chemical biology using unsaturated glycosyl donors. In past five years, we have reported several synthetic strategies with high stereoselectivity milder conditions compared previous works. particular, chemo-/regio- stereoselective O-glycosylation, C-glycosylation S-glycosylation could be achieved via palladium catalysis under open-air at room temperature. this Account, will introduce our research progress constructing four types of glycosides. 1 Introduction 2 Stereoselective Synthesis O-Glycosides 3 C-Glycosides 4 N-Glycosides 5 S-Glycosides 6 Conclusion

Language: Английский

Citations