Helical chiral 2-aminopyridinium ions: A new class of hydrogen bond donor catalysts

Norito Takenaka, Jinshui Chen, Burjor Captain, Robindro Singh Sarangthem, Appayee Chandrakumar

Research output: Contribution to journalArticle

130 Citations (Scopus)

Abstract

Helical chiral 2-aminopyridinium ions were designed as a significantly more acidic (active) dual hydrogen-bonding catalyst than commonly used (thio)urea-based systems. The helicene framework was specifically utilized to position an inherently chiral barrier on the hydrogen-bonding side of the catalyst. The catalyst reactivity and enantioselectivity were successfully demonstrated in additions of 4,7-dihydroindoles to nitroalkenes (0.5-2 mol % catalyst loadings, up to 98:2 er).

Original languageEnglish
Pages (from-to)4536-4537
Number of pages2
JournalJournal of the American Chemical Society
Volume132
Issue number13
DOIs
StatePublished - Apr 7 2010

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Hydrogen Bonding
Hydrogen
Hydrogen bonds
Ions
Catalysts
Urea
Enantioselectivity

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Helical chiral 2-aminopyridinium ions : A new class of hydrogen bond donor catalysts. / Takenaka, Norito; Chen, Jinshui; Captain, Burjor; Sarangthem, Robindro Singh; Chandrakumar, Appayee.

In: Journal of the American Chemical Society, Vol. 132, No. 13, 07.04.2010, p. 4536-4537.

Research output: Contribution to journalArticle

Takenaka, Norito ; Chen, Jinshui ; Captain, Burjor ; Sarangthem, Robindro Singh ; Chandrakumar, Appayee. / Helical chiral 2-aminopyridinium ions : A new class of hydrogen bond donor catalysts. In: Journal of the American Chemical Society. 2010 ; Vol. 132, No. 13. pp. 4536-4537.
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