Login / Signup

Stereoselective C-Aryl Glycosylation by Catalytic Cross-Coupling of Heteroaryl Glycosyl Sulfones.

Quanquan WangBoon Chong LeeNingXi SongMing Joo Koh
Published in: Angewandte Chemie (International ed. in English) (2023)
Stereoselective C-glycosylation reactions are increasingly gaining attention in carbohydrate chemistry because they enable glycosyl precursors, readily accessible as anomeric mixtures, to converge to a single diastereomeric product. However, controlling the stereochemical outcome through transition-metal catalysis remains challenging, and methods that leverage bench-stable heteroaryl glycosyl sulfone donors to facilitate glycosylation are rare. Herein, we show two complementary nonprecious metal catalytic systems, based on iron or nickel, which are capable of promoting efficient C-C coupling between heteroaryl glycosyl sulfones and aromatic nucleophiles or electrophiles through distinct mechanisms and modes of activation. Diverse C-aryl glycosides were secured with excellent selectivity, scope, and functional-group compatibility, and reliable access to both α and β isomers was possible for key sugar residues.
Keyphrases
  • transition metal
  • ionic liquid
  • crystal structure
  • room temperature
  • amino acid
  • drug discovery
  • carbon nanotubes
  • visible light