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

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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… Click to show full abstract

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.

Keywords: addition phosphonyl; phosphonyl radicals; dearomative addition; via dearomative; spirocyclic phosphonoindolines

Journal Title: Organic letters
Year Published: 2019

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