Synthesis of Spiroindenes via Palladium Catalysis Using Oxabicycles as Acetylene Surrogates

We report the palladium-catalyzed synthesis of spiroindenes using oxabicycles as acetylene surrogates. This protocol allows for the synthesis of a diverse library of heterocyclic-tethered spiroindenes. Preliminary results using enantioenriched oxabicycles as chiral auxiliaries allow for the synthesis of enantioenriched spiroindenes. The formation of unusual 6-<i>endo</i>-<i>trig</i> naphthyl side products is observed for substrates with proximal Lewis basic nitrogens.