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

来源：

ORGANIC LETTERS | 2020年 / 22卷 / 03期

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

页码：1144 / 1148

页数：5

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