Chiral Brønsted Acid Catalyzed Enantioselective Friedel–Crafts Reaction of Indoles and α‐Aryl Enamides: Construction of Quaternary Carbon Atoms

2007/06/22 by Yi‐Xia Jia, Jun Zhong, Shou‐Fei Zhu +2 · 1 citation
Chemistry · #Synthesis and Catalytic Reactions #Asymmetric Synthesis and Catalysis #Catalytic C–H Functionalization Methods

paper · doi:10.1002/anie.200701067

openalex publication_date 2007/06/22 · openalex created_date 2016/06/24 · openalex updated_date 2026/06/26

Abstract

S express: Quaternary carbon atoms are constructed in excellent yields with high enantioselectivities by a highly efficient chiral Brønsted acid catalyzed Friedel–Crafts reaction of indoles and α-aryl enamides (see scheme). The presence of H atoms on the N atoms of both the indole and enamide moieties is essential for the reaction to occur. The indole molecule attacks from the Re face to give S-configured products.

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• Electrophilic aromatic substitution [wikipedia]

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