Highly Stereospecific Cross-Coupling Reactions of Anomeric Stannanes for the Synthesis of C-Aryl Glycosides

被引：127
|
作者：
Zhu, Feng [1 ]
Rourke, Michael J. [1 ]
Yang, Tianyi [1 ]
Rodriguez, Jacob [1 ]
Walczak, Maciej A. [1 ]
机构：
[1] Univ Colorado, Dept Chem & Biochem, Campus Box 215, Boulder, CO 80309 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2016年 / 138卷 / 37期
关键词：
STEREOSELECTIVE-SYNTHESIS; ALKYL; BIOSYNTHESIS; NUCLEOSIDES; INHIBITOR; DISCOVERY; REAGENTS;
D O I：
10.1021/jacs.6b07891
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
We demonstrate that configurationally stable anomeric stannanes undergo a stereospecific cross coupling reaction with aromatic halides in the presence of a palladium catalyst with exceptionally high levels of stereocontrol. In addition to a broad substrate scope (>40 examples), this reaction eliminates critical problems inherent to nudeophilic displacement methods and is applicable to (hetero)aromatics, peptides, pharmaceuticals, common monosaccharides, and saccharides containing free hydroxyl groups.
引用
收藏
页码：12049 / 12052
页数：4
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