Other Methods
Why we were doing this chemistry
Known Methodology
Summary of Results

We made our discovery while preparing the starting endoxide, 1, shown below, for a novel synthesis of the benz[f]isoindole skeleton. We've found that the endoxide reacts with mesoionic munchnones, 2, prepared by the in situ dehydration of the corresponding amino acid, to give a 1,3-dipolar cycloadduct, 3. This adduct readily loses CO2 to yeild a second 1,3-dipolar cycloadduct, 4, which then undergoes a proton shift rather then react intermolecularly to compound 5. The stable intermediate thus formed is then easily elaborated to the benz[f]isoindole, 6, by dehydration.