Chiral Brønsted acid catalyzed asymmetric Friedel–Crafts alkylation reaction of indoles with α,β-unsaturated ketones: short access to optically active 2- and 3-substituted indole derivatives

Tsubasa Sakamoto; Junji Itoh; Keiji Mori; Takahiko Akiyama

doi:10.1039/C0OB00197J

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Organic & Biomolecular Chemistry

Issue 23, 2010

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Chiral Brønsted acid catalyzed asymmetric Friedel–Crafts alkylation reaction of indoles with α,β-unsaturated ketones: short access to optically active 2- and 3-substituted indole derivatives

Tsubasa Sakamoto , Junji Itoh , Keiji Mori and Takahiko Akiyama

Org. Biomol. Chem., 2010,8, 5448-5454

DOI: 10.1039/C0OB00197J
Received 02 Jun 2010, Accepted 06 Aug 2010
First published on the web 28 Sep 2010

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The asymmetric Friedel–Crafts alkylation reaction of indoles with α,β-unsaturated ketones catalyzed by chiral phosphoric acid is reported. A wide range of indoles and 4,7-dihydroindoles were allowed to react with α,β-unsaturated ketones to give the corresponding 1,4-adducts in good to high chemical yields and with excellent enantioselectivities.