Palladium(ii)-catalyzed stereoselective synthesis of C-glycosides from glycals with diaryliodonium salts

Org Biomol Chem. 2020 Mar 25;18(12):2242-2251. doi: 10.1039/d0ob00247j.

Abstract

An efficient palladium(ii) mediated C-glycosylation of glycals with diaryliodonium salts is described, providing a new strategy for the synthesis of 2,3-dideoxy C-aryl glycosides with excellent stereoselectivity. The C-glycosylation of a diverse range of glycals, including d-glucal, d-galactal, d-allal, l-rhamnal, l-fucal, l-arabinal, d-maltal, and d-lactal, occurred effectively and the corresponding C-glycosides were obtained in moderate to good yields. This protocol is commended as a significant addition to the field of carbohydrate chemistry due to the rich functional group compatibility, broad range of substrate scope and exceptional α-stereoselectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Ethers, Cyclic / chemistry*
  • Glycosides / chemical synthesis*
  • Glycosides / chemistry
  • Glycosylation
  • Palladium / chemistry*
  • Polysaccharides / chemistry
  • Salts / chemistry
  • Stereoisomerism

Substances

  • C-glycoside
  • Ethers, Cyclic
  • Glycosides
  • Polysaccharides
  • Salts
  • Palladium