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Copper(I)-Catalyzed Dearomative (3+2) Cycloaddition of 3-Nitroindoles with Propargylic Nucleophiles: a Straightforward Entry for The Preparation of Cyclopenta[b]indolines

preprint
submitted on 26.12.2019 and posted on 27.12.2019 by 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.

History

Email Address of Submitting Author

maxime.vitale@chimieparistech.psl.eu

Institution

Institute of Chemistry for Life and Health Science

Country

FRANCE

ORCID For Submitting Author

0000-0002-6740-2472

Declaration of Conflict of Interest

none

Version Notes

First version prior submission

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