Oxidant-Controlled Heck-Type C-Glycosylation of Glycals with Arylboronic Acids: Stereoselective Synthesis of Aryl 2-Deoxy-C-glycosides

被引：115

作者：

Xiong, De-Cai

Zhang, Li-He

Ye, Xin-Shan ^{[1
]}

机构：

[1] Peking Univ, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 08期

基金：

中国国家自然科学基金;

关键词：

COUPLING REACTIONS; GLYCOSIDATION; DEPROTECTION; ARYLATION;

D O I：

10.1021/ol900273d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Oxidative Heck-type C-glycosylations of glycals with various arylboronic acids using Pd(OAc)(2) as catalyst in the presence of oxidant were developed. The corresponding ketone, enol ether, and enone types of C-glycosides were predictably obtained with benzoquinone (BQ), Cu(OAc)(2)/O-2, and 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as oxidants, respectively. This method provides a simple, mild, and stereoselective synthesis of aryl 2-deoxy-C-glycosides.

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页码：1709 / 1712

页数：4

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