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

15 April 2019, Version 1
Working Paper
This content is a preprint and has not undergone peer review at the time of posting.

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.

Keywords

indole
dearomatization spiroindolines
aminophosphonates

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Version History

Apr 15, 2019 Version 1

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The content is available under CC BY NC ND 4.0 [opens in a new tab]

DOI

10.26434/chemrxiv.7988033.v1
D O I: 10.26434/chemrxiv.7988033.v1 [opens in a new tab]

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”)

Author’s competing interest statement

No conflict of interest

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