Open-Air Stereoselective Construction of C-Aryl Glycosides

被引:30
|
作者
Lai, Mengnan [1 ]
Othman, Karwan Abdulmajed [1 ,2 ]
Yao, Hui [1 ]
Wang, Qiuyuan [1 ]
Feng, Yongkui [1 ]
Huang, Nianyu [1 ]
Liu, Mingguo [1 ]
Zou, Kun [1 ]
机构
[1] China Three Gorges Univ, Coll Biol & Pharmaceut Sci, Hubei Key Lab Nat Prod Res & Dev, Yichang 443002, Peoples R China
[2] Koya Univ, Fac Engn, Dept Mfg & Ind Engn, Koya 45001, Iraq
基金
中国国家自然科学基金;
关键词
GLYCOSYLATION; GLYCALS; GALACTOSYLCERAMIDE; CATALYSIS; DESIGN;
D O I
10.1021/acs.orglett.9b04665
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new methodology of stereoselective C-glycosylation has been developed with 3,4-O-carbonate glycals and boronic acids, catalyzed by 1,2-bis(phenylsulfinyl)ethane palladium(II) acetate under open-air conditions at room temperature. This mild method is simple in operation, wide in substrate range, and tolerant in alcoholic/phenolic hydroxyl and amino groups. High to excellent yields were observed for all substrates tested, with the driving force mainly contributed by decarboxylation. Meanwhile, the high 1,4-trans-selectivity was achieved by steric effects as proposed.
引用
收藏
页码:1144 / 1148
页数:5
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