InBr3-catalyzed glycosidation of glycals with arylamines: an alternative approach to access 4-aminocyclopent-2-enones.
InBr3-catalyzed glycosidation of glycals with arylamines: an alternative approach to access 4-aminocyclopent-2-enones.
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DOI：
10.1021/jo200243d
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发表时间：
2011-03
期刊：
影响因子：
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通讯作者：
Fulong Li;C. Ding;Meining Wang;Qizheng Yao;A. Zhang
中科院分区：
文献类型：
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作者：
Fulong Li;C. Ding;Meining Wang;Qizheng Yao;A. Zhang
为了将副产物转化为主要产品，开发了一种获得生物活性4-氨基环戊烯-2-烯酮的新策略。这些化合物最初被鉴定为副产物，但当以3，5-二甲基吡喃-3，4-二醇7a为底物，30%InBr(3)为催化剂时，这些化合物成为主要产物。在该反应中可以使用芳基或杂芳胺以及各种取代的糖基，并以中等到较好的产率得到相应的4-氨基环戊烯-2-酮。这些化合物可进一步用于制备4-氨基碳环核苷。
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% InBr(3) 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.