Silver-Promoted Nazarov-like Reaction of Dichlorovinylcyclopropanes

Significance

Cyclopentenone is a very common ring system in natural products possessing biological activity, therefore new methods of its formation have attracted a lot of attention. The authors developed an original approach to the synthesis of halopentenones, based on a new silver-catalyzed ring-opening-cyclization tandem reaction of readily available alkenyl dichlorocyclopropanes. Since cyclopentenone adducts can be easily modified, this method allows a simple construction of polyfunctionalized cyclopentanone derivatives from acyclic precursors. The presence of an aryl moiety in the molecule gives access to polycyclic compounds.