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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, 13:21 and posted on 15.04.2019, 16:29 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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