Mild Cu(OTf)2-Mediated C-Glycosylation with Chelation-Assisted Picolinate as a Leaving Group | Zendy

Wenjing Ye | Zendy; Christopher Μ. Stevens | Zendy; Peng Wen | Zendy; Christopher J. Simmons | Zendy; Weiping Tang | Zendy

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Mild 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 -

the 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.

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