Chiral Brønsted acid-catalyzed enantioselective friedel-crafts reaction of 4,7-dihydroindoles with trifluoromethyl ketones

Teng Wang, Guang Wu Zhang, Yuou Teng, Jing Nie, Yan Zheng, Jun An Ma

Research output: Contribution to journalArticlepeer-review

40 Scopus citations

Abstract

In the presence of chiral phosphoric acid, an enantioselective Friedel-Crafts reaction of 4,7-dihydroindoles with aromatic trifluoromethyl ketones and ethyl 4,4,4-trifluoroacetoacetate has been realized. A series of 2-substituted 4,7-dihydroindoles with a trifluoromethylated tertiary alcohol moiety were obtained in 45-95% yields with 60-93% ee. Furthermore, 2-functionalized indole derivatives could be produced through a one-pot process.

Original languageEnglish (US)
Pages (from-to)2773-2777
Number of pages5
JournalAdvanced Synthesis and Catalysis
Volume352
Issue number16
DOIs
StatePublished - Nov 2 2010

Keywords

  • 4,7-dihydroindoles
  • Brønsted acids
  • Friedel-Crafts reaction
  • enantioselectivity
  • trifluoromethyl-substituted compounds

Fingerprint Dive into the research topics of 'Chiral Brønsted acid-catalyzed enantioselective friedel-crafts reaction of 4,7-dihydroindoles with trifluoromethyl ketones'. Together they form a unique fingerprint.

Cite this