Mild cu(Otf)2-mediated C-glycosylation with chelation-assisted picolinate as a leaving group

Article abstract of DOI:10.1021/acs.joc.0c01041

C-Glycosylation reactions of glycosyl picolinates with allyltrimethylsilane or silyl enol ethers were developed. Picolinate as a chelation-assisted leaving group could be activated by Cu(OTf)₂ and avoided the use of harsh Lewis acids. The glycosylations were operated under mild neutral conditions and gave the corresponding C-glycosides in up to 95% yield with moderate to excellent stereoselectivities.