Regio‐ and Enantioselective Iridium‐Catalyzed N‐Allylation of Indoles and Related Azoles with Racemic Branched Alkyl‐Substituted Allylic Acetates

Cyclometallated π‐allyliridium C,O‐benzoates modified with (S)‐tol‐BINAP, which are stable to air, water, and SiO2, catalyze highly enantioselective N‐allylations of indoles and related azoles. This reaction complements previously reported metal‐catalyzed indole allylations in that complete levels o...

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Bibliographic Details
Published in:Angewandte Chemie 2019-06, Vol.131 (23), p.7844-7848
Main Authors: Kim, Seung Wook, Schempp, Tabitha T., Zbieg, Jason R., Stivala, Craig E., Krische, Michael J.
Format: Article
Language:English
Subjects:
Acetates
Acetic acid
Allyl compounds
Allylische Alkylierung
Aminierung
Azoles
Benzoates
Benzoic acid
C-N-Bindungsbildung
Chemical reactions
Chemistry
Enantiomers
Enantioselektive Reaktionen
Heterocyclic compounds
Indoles
Iridium
Regioselectivity
Silicon dioxide
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Summary:Cyclometallated π‐allyliridium C,O‐benzoates modified with (S)‐tol‐BINAP, which are stable to air, water, and SiO2, catalyze highly enantioselective N‐allylations of indoles and related azoles. This reaction complements previously reported metal‐catalyzed indole allylations in that complete levels of N versus C3 and branched versus linear regioselectivity are observed. Immer an der richtigen Stelle: Cyclometallierte und mit (S)‐tol‐BINAP modifizierte π‐Allyliridium‐C,O‐benzoate – stabil in Luft, Wasser und SiO2 – katalysieren hoch enantioselektiv N‐Allylierungen von Indolen und anderen Azolen. Die Reaktion ergänzt vorherige metallkatalysierte Indol‐Allylierungen insofern, als vollständige Regioselektivität in Bezug auf N vs. C3 und verzweigt vs. linear erreicht wird.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201902799