Copper(I)-Catalyzed Dearomative (3 + 2) Cycloaddition of 3-Nitroindoles with Propargylic Nucleophiles: An Access to
Johanne Ling1, David Mara1, Baptiste Roure1
1Institute of Chemistry for Life and Health Sciences, PSL Université Paris, CNRS, Chimie ParisTech., 11 rue Pierre et Marie Curie, 75005 Paris, France.
Abstract:
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. The proof of concept that an enantioselective version of this reaction is accessible by employing chiral phosphorous ligands was obtained. A mechanism proposal is given based on kinetic studies.
More Related Videos
08:12A Two-Step Protocol for Umpolung Functionalization of Ketones Via Enolonium Species
Published on: August 16, 2018
10:17Efficient Construction of Drug-like Bispirocyclic Scaffolds Via Organocatalytic Cycloadditions of α-Imino γ-Lactones and Alkylidene Pyrazolones
Published on: February 7, 2019
Related Concept Videos
Cycloaddition Reactions: Overview
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
Cycloaddition Reactions: MO Requirements for Thermal Activation
Cyclohexenones via Michael Addition and Aldol Condensation: The Robinson Annulation
ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH3
Nucleophilic Aromatic Substitution: Elimination–Addition
