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 Bit 2017
Accepted
16 Elb 2017
First published
17 Elb 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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements