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Vincent Phosphonoindolines.pdf (970.14 kB)

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

preprint
submitted on 12.04.2019 and posted on 15.04.2019 by Dmytro Ryzakhov, Maxime Jarret, Jean Pierre Baltaze, Régis Guillot, Cyrille Kouklovsky, Guillaume Vincent
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.

Funding

DR thanks the Ministère de l’Enseignement Supérieur, de la Recherche et de l’Innovation (MESRI) for a PhD fellowship.

ANR-17-CE07-0050 (“ArDCo”)

History

Email Address of Submitting Author

guillaume.vincent@u-psud.fr

Institution

Université Paris Sud

Country

France

ORCID For Submitting Author

0000-0003-3162-1320

Declaration of Conflict of Interest

No conflict of interest

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