Issue 7, 2017

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
23 3 2017
Accepted
16 4 2017
First published
17 4 2017

Org. Chem. Front., 2017,4, 1407-1410

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, 4, 1407 DOI: 10.1039/C7QO00229G

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