Chiral phosphoric acid-catalyzed enantioselective aza-Friedel-Crafts reaction of indoles

Masahiro Terada, Shigeko Yokoyama, Keiichi Sorimachi, Daisuke Uraguchi

Research output: Contribution to journalArticle

138 Citations (Scopus)

Abstract

A highly enantioselective 1,2-aza-Friedel-Crafts reaction of N-tert-butyldimethylsilylindole with N-tert-butoxycarbonyl aromatic imines is demonstrated using a BINOL-derived monophosphoric acid catalyst. The present approach provides efficient access to 3-indolylmethaneamines with aryl substituents in excellent enantioselectivities (up to 98% ee). An inversion in the sense of enantioselection was found between monophosphoric acid catalysts bearing different substituents introduced at the 3,3′-position of binaphthyl backbone. We also calculated the three-dimensional structure of the monophosphoric acid catalysts to speculate on the inversion of the stereochemical outcome.

Original languageEnglish
Pages (from-to)1863-1867
Number of pages5
JournalAdvanced Synthesis and Catalysis
Volume349
Issue number11-12
DOIs
Publication statusPublished - 2007 Aug 1

Keywords

  • Asymmetric catalysis
  • Brønsted acid
  • Enantioselectivity
  • Friedel-Crafts reaction
  • Organic catalysis
  • Phosphoric acid

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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