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

1 Citation (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

Fingerprint

Friedel-Crafts reaction
bifonazole
Phenols
Antifungal agents
Catalysts
Acids
Antifungal Agents
Enantioselectivity
diphosphoric acid

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

Cite this

Chiral pyrophosphoric acid catalysts for the para-selective and enantioselective aza-friedel-crafts reaction of phenols. / Okamoto, Haruka; Toh, Kohei; Mochizuki, Takuya; Nakatsuji, Hidefumi; Sakakura, Akira; Hatano, Manabu; Ishihara, Kazuaki.

In: Synthesis (Germany), Vol. 50, No. 23, 01.01.2018, p. 4577-4590.

Research output: Contribution to journalArticle

Okamoto, Haruka ; Toh, Kohei ; Mochizuki, Takuya ; Nakatsuji, Hidefumi ; Sakakura, Akira ; Hatano, Manabu ; Ishihara, Kazuaki. / Chiral pyrophosphoric acid catalysts for the para-selective and enantioselective aza-friedel-crafts reaction of phenols. In: Synthesis (Germany). 2018 ; Vol. 50, No. 23. pp. 4577-4590.
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