The iridium-catalysed reductive coupling reaction of tertiary lactams/amides with isocyanoacetates†,Organic Chemistry Frontiers

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The iridium-catalysed reductive coupling reaction of tertiary lactams/amides with isocyanoacetates†
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2018-05-17 00:00:00 , DOI: 10.1039/c8qo00312b
Xiu-Ning Hu _{1,

2,

3,

4,

5} , Tai-Long Shen _{1,

2,

3,

4,

5} , Dong-Cheng Cai _{1,

2,

3,

4,

5} , Jian-Feng Zheng _{1,

2,

3,

4,

5} , Pei-Qiang Huang _{1,

2,

3,

4,

5}

Affiliation

Catalytic C–C bond forming methods for the one-pot transformation of amides into other classes of compounds are highly demanding. In this report, we demonstrate the catalytic reductive addition of isocyanoacetates to tertiary lactams/amides to produce 5-methoxyoxazoles, including N-heterocyclic substituted oxazoles and sterically hindered amino oxazoles that are difficult to obtain by traditional oxazole-forming Ugi-type reactions. This one-pot procedure involves the Ir-catalysed partial reduction of lactams/amides and the sequential chemoselective addition of the isocyanide group in isocyanoacetates.

中文翻译：

铱催化的内酰胺/酰胺与异氰基乙酸盐的还原偶联反应†

对于将酰胺一锅转化为其他类型化合物的催化CC键形成方法提出了很高的要求。在此报告中，我们证明了将异氰基乙酸酯催化还原加成到叔内酰胺/酰胺上可生成5-甲氧基恶唑，包括N-杂环取代的恶唑和空间受阻的氨基恶唑，这些是传统的形成恶唑的Ugi型反应难以获得的。此一锅法涉及内酰胺/酰胺的Ir催化部分还原，以及异氰酸酯中异氰酸酯基团的顺序化学选择性加成。

更新日期：2018-05-17

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