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

J Am Chem Soc. 2010 Apr 7;132(13):4536-7. doi: 10.1021/ja100539c.


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).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aminopyridines / chemistry*
  • Aza Compounds / chemical synthesis
  • Aza Compounds / chemistry
  • Catalysis
  • Crystallography, X-Ray
  • Hydrogen Bonding
  • Ions / chemistry
  • Models, Molecular
  • Molecular Structure
  • Stereoisomerism


  • Aminopyridines
  • Aza Compounds
  • Ions
  • alpha-aminopyridine