3 years ago

Strain-Promoted Nitration of 3-Cyclopropylideneprop-2-en-1-ones and the Application for the Synthesis of Pyrroles

Strain-Promoted Nitration of 3-Cyclopropylideneprop-2-en-1-ones and the Application for the Synthesis of Pyrroles
Jianfeng Xu, Huaping Xu, Zhengkai Chen, Hongjun Ren, Mengchao Jin, Yi Luo, Maozhong Miao
The tunable nucleophilic nitration of 3-cyclopropylideneprop-2-en-1-ones with cheap sodium nitrite is described. This transformation proceeds with the assistance of a strained cyclopropane ring and allows for a divergent route to various synthetically useful β,γ-dinitro or γ-mononitro adducts in high yields with exclusive regio- and stereoselectivity. Additionally, a wide array of valuable functionalized N-unprotected pyrroles is achieved from the resulting β,γ-dinitro compounds via reductive cyclization strategy.

Publisher URL: http://dx.doi.org/10.1021/acs.joc.7b02087

DOI: 10.1021/acs.joc.7b02087

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