InBr3-Catalyzed Glycosidation of Glycals with Arylamines: An Alternative Approach To Access 4-Aminocyclopent-2-enones

详细信息    查看全文

• 作者：Fulong Li ; Chunyong Ding ; Meining Wang ; Qizheng Yao ; Ao Zhang
• 刊名：Journal of Organic Chemistry
• 出版年：2011
• 出版时间：April 15, 2011
• 年：2011
• 卷：76
• 期：8
• 页码：2820-2827
• 全文大小：911K
• 年卷期：v.76,no.8(April 15, 2011)
• ISSN：1520-6904

文摘

To turn side products into major products, a novel strategy to access biologically active 4-aminocyclopent-2-enones was developed. These compounds were originally identified as side products but became major products when 3,5-dimethylpyran-3,4-diol 7a was used as the substrate and 30% InBr₃ as the catalyst. Aryl- or heteroarylamines as well as variously substituted glycals can be used in this reaction, and the corresponding 4-aminocyclopent-2-enones were obtained in moderate to good yields. These compounds can be further used to prepare 4-aminocarbocyclic nucleosides.