Tandem directed lithiations of N-Boc-1,2-dihydropyridines toward highly functionalized 2,3-dihydro-4-pyridones

Org Lett. 2005 Dec 8;7(25):5661-4. doi: 10.1021/ol052313a.


[chemical reaction: see text]. Sequential tandem directed lithiations of an N-Boc-4-methoxy-1,2-dihydropyridine have been achieved, leading to C-5,C-6 disubstituted dihydropyridones on acidic workup. The chlorine atom of the dihydropyridone products can in turn be substituted giving rise to diverse substituents at C-6.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Catalysis
  • Hydrocarbons, Chlorinated / chemical synthesis*
  • Hydrocarbons, Chlorinated / chemistry
  • Lithium / chemistry*
  • Molecular Structure
  • Pyridines / chemistry*
  • Pyridones / chemical synthesis*
  • Pyridones / chemistry*


  • Hydrocarbons, Chlorinated
  • Pyridines
  • Pyridones
  • Lithium