Enantioselective Friedel-Crafts Alkylation Reaction of Indoles with α-Trifluoromethylated β-Nitrostyrenes Catalyzed by Chiral BINOL Metal Phosphate

Ignacio Ibáñez, Mio Kaneko, Yuto Kamei, Ryosuke Tsutsumi, Masahiro Yamanaka, Takahiko Akiyama

Research output: Contribution to journalArticlepeer-review

19 Citations (Scopus)

Abstract

An efficient enantioselective Friedel-Crafts alkylation reaction of indoles with α-CF3-substituted β-nitrostyrenes is disclosed. The key to success is the use of a chiral calcium BINOL bis(phosphate) complex as a Lewis acid catalyst. The reaction gives access to a wide variety of optically active indoles bearing trifluoromethylated all-carbon quaternary stereocenter (up to 20 examples) in high yields (up to 99%) with excellent enantioselectivities (up to 98%) under mild reaction conditions. Nonactivated α-alkyl-β-nitrostyrenes also participated in the Friedel-Crafts alkylation reaction successfully.

Original languageEnglish
Pages (from-to)6903-6909
Number of pages7
JournalACS Catalysis
Volume9
Issue number8
DOIs
Publication statusPublished - 2019 Aug 2
Externally publishedYes

Keywords

  • Friedel-Crafts alkylation
  • Indole
  • metal chiral phosphate
  • nitroalkene
  • quaternary carbon center

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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