Pot-Economical Synthesis of Fluorinated Pyrrolizinone Derivatives

A new family of fluorinated dihydropyrrolizinones has been synthesized starting from fluorinated enamino amides and aliphatic conjugated ketones. The reaction comprises a cross metathesis reaction followed by a tandem cycloaromatization/ enamine hydrolysis/ intramolecular Friedel-Crafts alkylation sequence. This pot-economical process takes place in good yields (35-67%), taking into account that it consists of four consecutive reactions. Aromatic enones are also good partners for this protocol although, in this case, the cross metathesis reaction has to be performed in a separated step.