Why we were doing this
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.