Synthesis of 3,3-Spirocyclic-2-Phosphono-Indolines via a Dearomative Addition of Phosphonyl Radicals to Indoles

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This paper describes a method to synthesize trans-3,3-spirocyclic-2-phosphonoindolines through the dearomative addition of phosphonyl radicals to indoles under oxidative conditions.

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Abstract

We report the diastereoselective synthesis of alpha-aminophosphonates derivatives embedded in a spirocyclic indolines. Our method proceeds via the dearomative addition of phosphonyl radicals at the C2-position of the indole nucleus in oxidative conditions followed by the intramolecular trapping of the resulting carbocation before rearomatization. trans-3,3-Spirocyclic-2-phosphonoindolines were thus obtained.

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europepmc
last seen: 2026-05-19T01:45:01.086888+00:00
unpaywall
last seen: 2026-06-02T02:00:03.124865+00:00
License: CC-BY-NC-ND-4.0