Stereoselective Rearrangement of Trichloroacetimidates: Application to the Synthesis of α-Glycosyl Ureas

被引：20
|
作者：
Park, Nathaniel H. [1 ]
Nguyen, Hien M. [1 ]
机构：
[1] Montana State Univ, Dept Chem & Biochem, Bozeman, MT 59717 USA
来源：
ORGANIC LETTERS | 2009年 / 11卷 / 11期
关键词：
O-GLYCOSYL; AMINOGLYCOSIDE; ANTIBIOTICS; WATER; OLIGOSACCHARIDES; DISACCHARIDES; CARBAMATE; DESIGN; MODE; SITE;
D O I：
10.1021/ol900670a
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A new method for the stereoselective synthesis of alpha-glycosyl ureas, via nickel-catalyzed [1,3]-rearrangement of glycosyl trichloroacetimidates, has been developed. The alpha-stereoselectivity at the anomeric carbon of the resulting trichloroacetamides depends on the nature of the cationic nickel catalyst. This method is applicable to a number of trichloroacetimidate substrates. The alpha-glycosyl trichloroacetamides can be directly converted into alpha-glycosyl ureas in the presence of amines. In all cases, the stereochemical integrity at the urea linkages remains intact.
引用
收藏
页码：2433 / 2436
页数：4
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