Ligand‐Controlled Stereoselective Synthesis of 2‐Deoxy‐β‐C‐glycosides by Cobalt Catalysis DOI

Bingxue Liu,

Deguang Liu, Xianle Rong

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(22)

Published: March 17, 2023

2-Deoxy-β-C-glycosides represent an important class of carbohydrates that are present in many bioactive molecules. However, owing to the lack substituents at C2 position, stereoselective synthesis 2-deoxy-β-C-glycosides is highly challenging. Herein, we report a ligand-controlled C-alkyl glycosylation reaction access 2-deoxy-β-C-alkyl glycosides from readily available glycals and alkyl halides. This method exhibits broad substrate scope excellent diastereoselectivity under very mild conditions. In addition, unprecedented stereodivergent 2-deoxy-C-ribofuranosides achieved using different chiral bisoxazoline ligands. Mechanistic studies suggest hydrometallation glycal with bisoxazoline-ligated Co-H species may be turnover-limiting stereodetermining step this transformation.

Language: Английский

Recent advances in transition-metal-catalyzed glycosyl cross-coupling reactions DOI Open Access

Anrong Chen,

Bo Yang, Zhenghong Zhou

et al.

Chem Catalysis, Journal Year: 2022, Volume and Issue: 2(12), P. 3430 - 3470

Published: Nov. 8, 2022

Language: Английский

Citations

45
Oxygen-vacancy-boosted visible light driven photocatalytic oxidative dehydrogenation of saturated N-heterocycles over Nb2O5 nanorods DOI

Yinpan Zhang,

Tao Song, Xin Zhou

et al.

Applied Catalysis B Environment and Energy, Journal Year: 2022, Volume and Issue: 316, P. 121622 - 121622

Published: June 11, 2022

Language: Английский

Citations

44
StereoselectiveC‐Aryl Glycosylation by Catalytic Cross‐Coupling of Heteroaryl Glycosyl Sulfones DOI

Quanquan Wang,

Boon Chong Lee,

NingXi Song

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(18)

Published: March 7, 2023

Stereoselective C-glycosylation reactions are increasingly gaining attention in carbohydrate chemistry because they enable glycosyl precursors, readily accessible as anomeric mixtures, to converge a single diastereomeric product. However, controlling the stereochemical outcome through transition-metal catalysis remains challenging, and methods that leverage bench-stable heteroaryl sulfone donors facilitate glycosylation rare. Herein, we show two complementary nonprecious metal catalytic systems, based on iron or nickel, which capable of promoting efficient C-C coupling between sulfones aromatic nucleophiles electrophiles distinct mechanisms modes activation. Diverse C-aryl glycosides were secured with excellent selectivity, scope, functional-group compatibility, reliable access both α β isomers was possible for key sugar residues.

Language: Английский

Citations

42
Recent development of stereoselective C-glycosylation via generation of glycosyl radical DOI Creative Commons
Titli Ghosh, Toshiki Nokami

Carbohydrate Research, Journal Year: 2022, Volume and Issue: 522, P. 108677 - 108677

Published: Sept. 17, 2022

Language: Английский

Citations

40
Ligand‐Controlled Stereoselective Synthesis of 2‐Deoxy‐β‐C‐glycosides by Cobalt Catalysis DOI

Bingxue Liu,

Deguang Liu, Xianle Rong

et al.

Angewandte Chemie International Edition, Journal Year: 2023, Volume and Issue: 62(22)

Published: March 17, 2023

2-Deoxy-β-C-glycosides represent an important class of carbohydrates that are present in many bioactive molecules. However, owing to the lack substituents at C2 position, stereoselective synthesis 2-deoxy-β-C-glycosides is highly challenging. Herein, we report a ligand-controlled C-alkyl glycosylation reaction access 2-deoxy-β-C-alkyl glycosides from readily available glycals and alkyl halides. This method exhibits broad substrate scope excellent diastereoselectivity under very mild conditions. In addition, unprecedented stereodivergent 2-deoxy-C-ribofuranosides achieved using different chiral bisoxazoline ligands. Mechanistic studies suggest hydrometallation glycal with bisoxazoline-ligated Co-H species may be turnover-limiting stereodetermining step this transformation.

Language: Английский

Citations

35