Issue 2, 2025

Catalytic enantioselective and site-specific Friedel–Crafts alkylation of 4-aminoindoles with β,γ-alkynyl-α-ketoimines for the synthesis of C7-functionalized indoles

Abstract

Chiral phosphoric acid-catalyzed enantioselective Friedel–Crafts alkylation of 4-aminoindoles with β,γ-alkynyl-α-ketoimines has been developed. A range of optically pure C7-functionalized indoles bearing a quaternary α-amino acid or trifluoromethylated tetrasubstituted alkylamine motif were obtained with up to 98% yield and 99% ee. This protocol effectively incorporates site-specific Friedel–Crafts alkylation at the C7 site of 4-aminoindoles and regio-specific quaternary stereocenter construction at the α-position of β,γ-alkynyl-α-ketoimines, and opens a new avenue to access chiral C7-functionalized indoles.

Graphical abstract: Catalytic enantioselective and site-specific Friedel–Crafts alkylation of 4-aminoindoles with β,γ-alkynyl-α-ketoimines for the synthesis of C7-functionalized indoles

Supplementary files

Article information

Article type
Research Article
Submitted
02 Oct 2024
Accepted
15 Nov 2024
First published
19 Nov 2024

Org. Chem. Front., 2025,12, 655-661

Catalytic enantioselective and site-specific Friedel–Crafts alkylation of 4-aminoindoles with β,γ-alkynyl-α-ketoimines for the synthesis of C7-functionalized indoles

L. Yang, X. Zhang, J. Liao, Y. Zhang, Z. Wang, Y. You, J. Zhao and W. Yuan, Org. Chem. Front., 2025, 12, 655 DOI: 10.1039/D4QO01856G

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