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. 2025 Apr 1;367(7):e202401536.
doi: 10.1002/adsc.202401536. Epub 2025 Feb 26.

Selectivity Rules for the Dearomative (3+2) Annulation Reaction Between Substituted Indoles and Oxyallyl Cations

Dhiman Saha  1 , Jimmy Wu  1
Affiliations

Selectivity Rules for the Dearomative (3+2) Annulation Reaction Between Substituted Indoles and Oxyallyl Cations

Dhiman Saha et al. Adv Synth Catal. .

Abstract

We report a collection of "selectivity rules" for the dearomative (3+2) annulation reaction between substituted indoles and oxyallyl cations. The application of these rules enables us to synthesize four different regioisomeric permutations of the annulation products in a stereoselective fashion. We demonstrated that these products could be further transformed into hexahydro- and tetrahydrocarbazoles by nucleophile-intercepted Beckmann fragmentation (NuBFr) and Beckmann fragmentation (BFr).

Keywords: carbazole; indole; oxyallyl cation; regioselective; stereoselective.

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