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

Published: June 21, 2024

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 on the benzene ring, has been limited often overlooked. This study presents a highly efficient organocatalytic protocol for synthesizing chiral indoles. The efficiency developed methodology is demonstrated by its broad substrate scope, excellent functional group tolerance, use only 1 mol% conjugated acid catalyst. Additionally, observed regioselectivity, gram-scale reaction, various follow-up transformations underscore potential method.

Language: Английский

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

Organic Letters, Journal Year: 2024, Volume and Issue: 26(33), P. 6993 - 6998

Published: Aug. 8, 2024

Chiral indoles annulated on the benzene ring are unique and significant in natural medicinal compounds. However, accessing these enantioenriched molecules has often been overlooked. The present study introduces an organocatalytic protocol to access compounds efficiently, demonstrated by substrate scope, functional group tolerance, using only 1 mol % of a chiral conjugated acid catalyst. Additionally, explores regioselectivity, gram-scale reactions, follow-up transformations, underscoring method's potential.

Language: Английский