Open AccessMild Cu(OTf)2-Mediated C-Glycosylation with Chelation-Assisted Picolinate as a Leaving Group
Author(s) -
Wenjing Ye,
Christopher Μ. Stevens,
Peng Wen,
Christopher J. Simmons,
Weiping Tang
Publication year - 2020
Publication title -
journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.2
H-Index - 228
eISSN - 1520-6904
pISSN - 0022-3263
DOI - 10.1021/acs.joc.0c01041
Subject(s) - chemistry , chelation , glycosylation , lewis acids and bases , yield (engineering) , glycosyl , silylation , glycosyl donor , leaving group , medicinal chemistry , glycoside , enol , stereochemistry , organic chemistry , catalysis , biochemistry , materials science , metallurgy
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.