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-endo-trig naphthyl side products is observed for substrates with proximal Lewis basic nitrogens.
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Jans et al. (2025) studied this question.
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