This synthesis reveals spirooxindole-γ-lactones formation via azaoxyallyl cations and 2-naphthols, indicating a new approach in organic synthesis.
All-carbon quaternary spirocyclic oxindoles are privileged frameworks. Here, we report an efficient strategy to access spirooxindole-γ-lactones by engaging transient oxindolyl azaoxyallyl cations with β-naphthols. Extension of the methodology to α-aryl halohydroxamates was also permitted. HFIP was the sole activator, which, besides generating an azaoxyallyl cation, also facilitates the crucial lactonization step.
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Mondal et al. (2025) studied this question.
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