Palladium-Catalyzed Decarboxylative Allylation/Wittig Reaction: Substrate-Controlled Synthesis of C-Vinyl Glycosides | Zendy

WeiLin Leng | Zendy; Hongze Liao | Zendy; Hui Yao | Zendy; Zi-En Ang | Zendy; ShaoHua Xiang | Zendy; XueWei Liu | Zendy

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Palladium-Catalyzed Decarboxylative Allylation/Wittig Reaction: Substrate-Controlled Synthesis of C-Vinyl Glycosides

Author(s) -

WeiLin Leng,

Hongze Liao,

Hui Yao,

Zi-En Ang,

ShaoHua Xiang,

XueWei Liu

Publication year - 2017

Publication title -

organic letters

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.94

H-Index - 239

eISSN - 1523-7060

pISSN - 1523-7052

DOI - 10.1021/acs.orglett.6b03697

Subject(s) - chemistry , wittig reaction , palladium , glycoside , catalysis , organic chemistry , substrate (aquarium) , combinatorial chemistry , oceanography , geology

A palladium-catalyzed one-pot Tsuji-Trost type decarboxylative allylation/Wittig reaction has been developed to synthesize C-vinyl glycosides. Screening of various aldehydes led to formation of β,(E)-selective C-vinyl glycosides with pyridyl group containing aldehydes and β,(Z)-selective C-vinyl glycosides with nonpyridyl aldehydes. A plausible mechanism is proposed based on the coordination effect of the aldehydes.

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