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Asymmetric synthesis of CF3- and indole-containing tetrahydro-β-carbolines via chiral spirocyclic phosphoric acid-catalyzed aza-Friedel–Crafts reaction

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Abstract

An enantioselective aza-Friedel–Crafts alkylation reaction of indoles with 1-trifluoromethyl-3,4-dihydro-β-carbolines catalyzed by a chiral spirocyclic phosphoric acid has been realized. This methodology provides a facile route to 1-trifluoromethyl-1-indole-substituted tetrahydro-β-carbolines featuring a CF3-containing quaternary stereocenter in considerable yields and good enantioselectivities.

Graphical abstract: Asymmetric synthesis of CF3- and indole-containing tetrahydro-β-carbolines via chiral spirocyclic phosphoric acid-catalyzed aza-Friedel–Crafts reaction

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Publication details

The article was received on 23 Mar 2017, accepted on 16 Apr 2017 and first published on 17 Apr 2017


Article type: Research Article
DOI: 10.1039/C7QO00229G
Citation: Org. Chem. Front., 2017, Advance Article
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    Asymmetric synthesis of CF3- and indole-containing tetrahydro-β-carbolines via chiral spirocyclic phosphoric acid-catalyzed aza-Friedel–Crafts reaction

    E. Xie, A. Rahman and X. Lin, Org. Chem. Front., 2017, Advance Article , DOI: 10.1039/C7QO00229G

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