Chiral pyrophosphoric acid catalysts for the para-selective and enantioselective aza-friedel-crafts reaction of phenols

Haruka Okamoto, Kohei Toh, Takuya Mochizuki, Hidefumi Nakatsuji, Akira Sakakura, Manabu Hatano, Kazuaki Ishihara

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

Chiral BINOL-derived pyrophosphoric acid catalysts were developed and used for the regio- and enantioselective aza-Friedel-Crafts reaction of phenols with aldimines. ortho/para-Directing phenols could react at the para-position selectively with moderate to good enantioselectivities. Moreover, the gram-scale transformation of a product into the key intermediate for the antifungal agent (R)-bifonazole was demonstrated.

Original languageEnglish
Pages (from-to)4577-4590
Number of pages14
JournalSynthesis (Germany)
Volume50
Issue number23
DOIs
Publication statusPublished - Jan 1 2018

Keywords

  • Aza-Friedel-Crafts reaction
  • Brønsted acid
  • Or-ganocatalyst
  • Phenol
  • Phosphoric acid
  • Pyrophosphoric acid
  • Regio-selectivity

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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