C-Glycopyranosyl styrene type compounds are valuable synthetic intermediates whose syntheses are known in rather lengthy procedures. Herein palladium-catalyzed cross-couplings of O-peracylated 2,6-anhydro-aldose tosylhydrazones with benzyl bromides were studied under thermic conditions in the presence of LiOtBu. The reactions gave the corresponding C-glycopyranosyl styrenes in up to 59% yields. The transformations represent a new, short synthetic sequence to get this type of glycomimetic compounds in 4–5 steps from a free aldose. (Figure presented.).
- Anhydro-aldose tosylhydrazones
- C−C coupling
ASJC Scopus subject areas
- Organic Chemistry