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

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

Published:2017 Issue:7 Volume:4 Page:1407-1410
ISSN:2052-4129
Container-title:Organic Chemistry Frontiers
language:en
Short-container-title:Org. Chem. Front.

Author:

Xie En¹²³⁴⁵,Rahman Abdul¹²³⁴⁵,Lin Xufeng¹²³⁴⁵^ORCID

Affiliation:

1. Laboratory of Asymmetric Catalysis and Synthesis

2. Department of Chemistry

3. Zhejiang University

4. Hangzhou 310027

5. China

Abstract

An enantioselective aza-Friedel–Crafts reaction of indoles with 1-trifluoromethyl-3,4-dihydro-β-carbolines has been developed to afford tetrahydro-β-carbolines with a CF₃- and indole-containing quaternary stereocenter by using chiral phosphoric acid catalysis.

Funder

National Natural Science Foundation of China

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2017/QO/C7QO00229G

Reference69 articles.

1. Simple indole alkaloids and those with a nonrearranged monoterpenoid unit

2. Simple indole alkaloids and those with a nonrearranged monoterpenoid unit

3. A β-Carboline Alkaloid from the Papua New Guinea Marine Sponge Hyrtios reticulatus