Enantioselective bromocyclization of 2-geranylphenols induced by chiral phosphite-urea bifunctional catalysts

Yasuhiro Sawamura, Yoshihiro Ogura, Hidefumi Nakatsuji, Akira Sakakura, Kazuaki Ishihara

Research output: Contribution to journalArticle

17 Citations (Scopus)

Abstract

Chiral phosphite-urea bifunctional catalysts have been developed for the enantioselective bromocyclization of 2-geranylphenols with N-bromophthalimide (NBP) for the first time. The chiral triaryl phosphite moiety activates NBP to generate a bromophosphonium ion. On the other hand, the urea moiety interacts with a hydroxyl group of the substrate through hydrogen bonding interactions. Enantioselectivity is effectively induced through two-point attractive interactions between the catalyst and the substrate.

Original languageEnglish
Pages (from-to)6068-6071
Number of pages4
JournalChemical Communications
Volume52
Issue number36
DOIs
Publication statusPublished - 2016

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Phosphites
Urea
Catalysts
Enantioselectivity
Substrates
Hydroxyl Radical
Hydrogen bonds
Ions
N-bromophthalimide

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Ceramics and Composites
  • Electronic, Optical and Magnetic Materials
  • Surfaces, Coatings and Films
  • Materials Chemistry
  • Metals and Alloys

Cite this

Enantioselective bromocyclization of 2-geranylphenols induced by chiral phosphite-urea bifunctional catalysts. / Sawamura, Yasuhiro; Ogura, Yoshihiro; Nakatsuji, Hidefumi; Sakakura, Akira; Ishihara, Kazuaki.

In: Chemical Communications, Vol. 52, No. 36, 2016, p. 6068-6071.

Research output: Contribution to journalArticle

Sawamura, Yasuhiro ; Ogura, Yoshihiro ; Nakatsuji, Hidefumi ; Sakakura, Akira ; Ishihara, Kazuaki. / Enantioselective bromocyclization of 2-geranylphenols induced by chiral phosphite-urea bifunctional catalysts. In: Chemical Communications. 2016 ; Vol. 52, No. 36. pp. 6068-6071.
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