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

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.