Sn-free Ni-catalyzed reductive coupling of glycosyl bromides with activated alkenes.
A mild, stereoselective method for the Ni-catalyzed synthesis of alpha-C-alkylglycosides is reported. This approach entails the reductive coupling of glycosyl bromides with activated alkenes at room temperature, with low alkene loading as an important feature. Diastereoselective coupling with 2-substituted acrylate derivatives was made possible through the use of 2,4-dimethyl-3-pentanol as a proton source.
Gong
Hegui
H
University of North Carolina at Chapel Hill, Department of Chemistry, Chapel Hill, North Carolina 27599, USA.
Andrews
R Stephen
RS
Zuccarello
Joseph L
JL
Lee
Stephen J
SJ
Gagné
Michel R
MR
D000475:Alkenes / Q000737:chemistry*; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D006027:Glycosides / Q000138:chemical synthesis* / Q000737:chemistry; D006842:Hydrocarbons, Brominated / Q000737:chemistry*; D015394:Molecular Structure; D009532:Nickel / Q000737:chemistry*
D000475:Alkenes; D006027:Glycosides; D006842:Hydrocarbons, Brominated; D009532:Nickel