Oxidative Heck reaction of glycals and aryl hydrazines: a palladium-catalyzed C-glycosylation.
An efficient Heck-type C-glycosylation of glycals via the C-N bond cleavage of aryl hydrazines has been developed. The flexibility of the reaction was tested by the substrate scope, consisting of glycals from different carbohydrate origins as well as aryl hydrazines with various substituents. Pure α-C-glycosides were obtained when (3R)-glycals were employed, whereas α,β mixtures were observed with (3S)-glycals.
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371.
Yaguang
Y
Bai
Le Mai Hoang
le MH
Kim
Hongze
H
Liao
Xue-Wei
XW
Liu
D002384:Catalysis; D006027:Glycosides / Q000737:chemistry*; D006031:Glycosylation; D006834:Hydrazines / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry*
D006027:Glycosides; D006834:Hydrazines; D010165:Palladium