Palladium(II)-Catalyzed Diastereoselective 2,3-Trans C(sp<sup>3</sup>)–H Arylation of Glycosides

Nicolas Probst, Gwendal Grelier, Slimane Dahaoui, Mouâd Alami, Vincent Gandon, Samir Messaoudi

ACS Catalysis · 2018 · 59 citations · 44 references

Concepts

Abstract

We report herein the diastereoselective C(sp 3 )–H arylation of glycosides. A wide range of β- and α-glycosides proved able to selectively undergo Pd(II)-catalyzed coupling with diverse aryl iodides to assemble a large library of functionalized 3-arylglycosylamides. DFT calculations were performed to elucidate the unexpected trans stereoselectivity of this reaction.

References

44