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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
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submitted on 12.04.2019 and posted on 15.04.2019by 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.