2006Journal of the American Chemical SocietyRequires access

Enantioselective Friedel−Crafts Reaction of Electron-Rich Alkenes Catalyzed by Chiral Brønsted Acid

Masahiro Terada, Keiichi Sorimachi

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Abstract

We present the first enantioselective catalysis of the Friedel−Crafts reaction via activation of electron-rich multiple bonds by a chiral Brønsted acid. The reaction of various indole derivatives with a broad range of substituted enecarbamates affords the corresponding Friedel−Crafts products in high yield and enantioselectivity.

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What this paper is about

We present the first enantioselective catalysis of the Friedel−Crafts reaction via activation of electron-rich multiple bonds by a chiral Brønsted acid. The reaction of various indole derivatives with a broad range of substituted enecarbamates affords the corresponding Friedel−Crafts products in high yield and enantioselectivity.

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Available abstract

We present the first enantioselective catalysis of the Friedel−Crafts reaction via activation of electron-rich multiple bonds by a chiral Brønsted acid. The reaction of various indole derivatives with a broad range of substituted enecarbamates affords the corresponding Friedel−Crafts products in high yield and enantioselectivity.

Key concepts: Friedel–Crafts reaction, Chemistry, Enantioselective synthesis, Brønsted–Lowry acid–base theory, Catalysis, Indole test, Yield (engineering), Organic chemistry

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