Synthesis of 3,3-Spirocyclic 2-Phosphonoindolines via a Dearomative Addition of Phosphonyl Radicals to Indoles - Archive ouverte HAL Accéder directement au contenu
Article Dans Une Revue Organic Letters Année : 2019

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

Résumé

The diastereoselective synthesis of α-amino phosphonate derivatives embedded in spirocyclic indolines is reported. The present 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.

Domaines

Chimie organique
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Dates et versions

hal-02322542 , version 1 (20-11-2020)

Identifiants

Citer

Dmytro Ryzhakov, Maxime Jarret, Jean-Pierre J.-P. Baltaze, Régis Guillot, Cyrille Kouklovsky, et al.. Synthesis of 3,3-Spirocyclic 2-Phosphonoindolines via a Dearomative Addition of Phosphonyl Radicals to Indoles. Organic Letters, 2019, 21 (13), pp.4986-4990. ⟨10.1021/acs.orglett.9b01516⟩. ⟨hal-02322542⟩
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