Regio- and Enantioselective N-Heterocyclic Carbene-Catalyzed Annulation of Aminoindoles Initiated by Friedel-Crafts Alkylation

21 June 2024, Version 1
This content is a preprint and has not undergone peer review at the time of posting.


Chiral annulated indoles are unique molecules with numerous examples of this structural motif in natural and medicinally relevant compounds. However, accessing these enantioenriched molecules, particularly indoles annulated on the benzene ring, has been limited and often overlooked. This study presents a highly efficient organocatalytic protocol for synthesizing chiral annulated indoles. The efficiency of the developed methodology is demonstrated by its broad substrate scope, excellent functional group tolerance, and the use of only 1 mol% of a chiral conjugated acid of catalyst. Additionally, the study of the observed regioselectivity, gram-scale reaction, and various follow-up transformations underscore the potential of this method.


N-heterocyclic carbene

Supplementary materials

Supporting Information
Reaction conditions optimization, experimental procedures and characterization data for all compounds, crystallographic data, description of computational methods, copies of 1H NMR, 13C NMR, 19F NMR, and copies of chiral HPLC.


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