Dearomatization of 3‐Nitroindoles by a Phosphine‐Catalyzed Enantioselective [3+2] Annulation Reaction

The dearomatization of 3‐nitroindoles through a chiral‐phosphine‐mediated [3+2] annulation reaction is described. This method makes use of readily available 3‐nitroindoles as an aromatic feedstock and rapidly delivers a wide range of cyclopentaindoline alkaloid scaffolds in a highly enantioselective...

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Bibliographic Details
Published in:Angewandte Chemie International Edition 2019-04, Vol.58 (16), p.5427-5431
Main Authors: Li, Kaizhi, Gonçalves, Théo P., Huang, Kuo‐Wei, Lu, Yixin
Format: Article
Language:English
Subjects:
[3+2] annulation
Chemical reactions
cyclopentaindolines
dearomatization
Enantiomers
nitroindoles
Organic chemistry
organocatalysis
Phosphine
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Summary:The dearomatization of 3‐nitroindoles through a chiral‐phosphine‐mediated [3+2] annulation reaction is described. This method makes use of readily available 3‐nitroindoles as an aromatic feedstock and rapidly delivers a wide range of cyclopentaindoline alkaloid scaffolds in a highly enantioselective manner. Notably, phosphine‐triggered cyclization has not been utilized previously in a dearomatization process. A disruptive influence: Variously substituted 3‐nitroindoles underwent dearomatization in a phosphine‐catalyzed asymmetric [3+2] annulation reaction with allenoates (see scheme). This method makes use of 3‐nitroindoles as a readily available aromatic feedstock and provides access to a wide range of cyclopentaindolines in a highly enantioselective manner.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.201900248