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submitted on 26.12.2019 and posted on 27.12.2019by Johanne Ling, David Mara, Baptiste Roure, Maxime Laugeois, Maxime Vitale
The copper(I)-catalyzed dearomatization of
3-nitroindoles with propargylic nucleophiles is described. In mild reaction
conditions, this original dearomative (3+2) cycloaddition process gives access to
a wide variety of cyclopenta[b]indolines
in good to excellent yields, with high functional group tolerance. Furthermore,
an enantioselective version of this reaction is reachable by employing chiral
phosphorous ligands. A mechanism proposal is given, based on kinetic studies.