Open AccessPalladium-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 , combinatorial chemistry
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.