Copper(I)-Catalyzed Dearomative (3 + 2) Cycloaddition of 3-Nitroindoles with Propargylic Nucleophiles: An Access to Cyclopenta[b]indolines | Zendy

Johanne Ling | Zendy; D. Duncan Mara | Zendy; Baptiste Roure | Zendy; Maxime Laugeois | Zendy; Maxime R. Vitale | Zendy

Open Access

Copper(I)-Catalyzed Dearomative (3 + 2) Cycloaddition of 3-Nitroindoles with Propargylic Nucleophiles: An Access to Cyclopenta[b]indolines

Author(s) -

Johanne Ling,

D. Duncan Mara,

Baptiste Roure,

Maxime Laugeois,

Maxime R. Vitale

Publication year - 2020

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.9b03459

Subject(s) - chemistry , nucleophile , cycloaddition , enantioselective synthesis , catalysis , copper , combinatorial chemistry , medicinal chemistry , stereochemistry , organic chemistry

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.

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