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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Published inAngewandte Chemie Vol. 131; no. 16; pp. 5481 - 5485
Main Authors Li, Kaizhi, Gonçalves, Théo P., Huang, Kuo‐Wei, Lu, Yixin
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 08.04.2019
Subjects
[3+2]-Anellierung
Chemical reactions
Chemistry
Cyclopentaindoline
Dearomatisierung
Enantiomers
Nitroindole
Organic chemistry
Organokatalyse
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. Ein störender Einfluss: Substituierte 3‐Nitroindole wurden in einer phosphinkatalysierten asymmetrischen [3+2]‐Anellierung mit Allenoaten dearomatisiert (siehe Schema). Das Verfahren nutzt 3‐Nitroindole als leicht verfügbare aromatische Rohstoffe und ermöglicht den Zugang zu einem breiten Spektrum von Cyclopentaindolinen auf hoch enantioselektive Weise.
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ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201900248