Regioselective Nitrative Cyclization of 1,6-Enynes with t-BuONO under Metal-Free Conditions,ACS Sustainable Chemistry & Engineering

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Regioselective Nitrative Cyclization of 1,6-Enynes with t-BuONO under Metal-Free Conditions
ACS Sustainable Chemistry & Engineering ( IF 7.1 ) Pub Date : 2018-10-04 00:00:00 , DOI: 10.1021/acssuschemeng.8b03752
Wen-Ting Wei ₁ , Wei-Wei Ying ₁ , Wen-Hui Bao ₁ , Le-Han Gao ₁ , Xu-Dong Xu ₁ , Yi-Ning Wang ₁ , Xiao-Xiao Meng ₁ , Gan-Ping Chen ₁ , Qiang Li ₂

Affiliation

A new pattern for nitrative cyclization of 1,6-enynes with t-BuONO has been reported for the synthesis of various 2-pyrrolidinone derivatives in 45–88% yields. This novel method is operationally simple and proceeds under very mild conditions without using any additives. The reaction pathway involves nitro radical addition toward an alkenyl group/5-exo-cyclization/H-abstraction sequence, allowing a highly regioselective and practical protocol toward the formation of new C–N and C–C bonds.

中文翻译：

在无金属条件下用t -BuONO进行1,6-烯炔的区域选择性硝化环化

已经报道了一种用叔-BuONO对1，6-烯炔进行硝化环化的新模式，用于合成各种2-吡咯烷酮衍生物，产率为45-88％。该新颖方法操作简单，并且在非常温和的条件下进行而无需使用任何添加剂。该反应途径涉及向烯基/ 5-外-环化/ H-抽象序列添加硝基自由基，从而为形成新的C-N和CC键提供了高度区域选择性和实用的方法。

更新日期：2018-10-04

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