Tandem epoxide or aziridine ring opening by azide/copper catalyzed [3+2] cycloaddition:: Efficient synthesis of 1,2,3-triazolo β-hydroxy or β-tosylamino functionality motif

被引：81
|
作者：
Kumaraswamy, Gullapalli [1 ]
Ankamma, Kukkadapu [1 ]
Pitchaiah, Arigala [1 ]
机构：
[1] Indian Inst Chem Technol, Div Organ Chem 3, Fine Chem Lab, Hyderabad 500007, Andhra Pradesh, India
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 25期
关键词：
D O I：
10.1021/jo701724f
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
[Graphics] A novel and practical procedure for the synthesis of small molecules possessing beta-hydroxy or N-tosylamino 1,2,3-triazole motif by azidation of epoxides or N-tosylaziridines with sodium azide followed by "click reaction" using eco-friendly PEG-400 as a reaction medium in the presence of 5 mol % of CuI is described. Enantiomerically pure epoxide and N-tosylaziridines were afforded in high yield with excellent ee values maintaining complete stereospecificity.
引用
收藏
页码：9822 / 9825
页数：4
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