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Gold-Catalyzed Addition-N-Boc Cleavage-Cyclization of N,O-Acetal with Ynamides for Construction of 6-(tert-Butyldimethylsilyl)oxy-tetrahydropyrrolo[1,2-c][1,3]oxazin-1-ones.
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-09-14 , DOI: 10.1021/acs.joc.0c01776
Yan-Xue Zhang 1, 2 , Ling-Yan Chen 1, 3 , Jian-Ting Sun 1, 2 , Chang-Mei Si 2 , Bang-Guo Wei 2
Affiliation  

A highly efficient gold-catalyzed approach between N,O-acetals and ynamides for the construction of 6-(tert-butyldimethylsilyl)oxy-tetrahydropyrrolo[1,2-c][1,3]oxazin-1-ones was developed. This reaction tolerated a wide range of substituted N,O-acetals and TsN-substituted ynamides, leading to novel heterocycles in moderate to good yields and with excellent diastereoselectivities (dr > 99:1).

中文翻译:

金催化的N,O-缩醛与酰胺的加成-N-Boc裂解-环化反应,生成6-(叔丁基二甲基甲硅烷基)氧基-四氢吡咯并[1,2-c] [1,3]恶嗪-1-酮。

提出了一种在NO-乙缩醛和乙酰胺之间的高效金催化方法,用于构建6-(丁基二甲基甲硅烷基)氧基-四氢吡咯并[1,2- c ] [1,3]恶嗪-1-酮。该反应可耐受各种取代的NO-乙缩醛和TsN取代的乙酰胺,从而以中等至良好的收率和极好的非对映选择性(dr> 99:1)产生新型杂环。
更新日期:2020-10-02
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