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