One-pot tandem double-aldol reaction/aza-addition of acetylacetamides and o-phthalaldehyde leading to spiroindan-2,2'-pyrrolidines

Org Lett. 2009 Jan 1;11(1):93-6. doi: 10.1021/ol802507y.

Abstract

A novel domino reaction based on o-phthalaldehyde and 3-oxo-N-arylbutanamide 1 has been developed which allows one-pot and efficient synthesis of structurally complex spiroindan-2,2'-pyrrolidines 2 and 3 with complete regioselectivity and high stereoselectivity from acyclic precursors.

MeSH terms

  • Acetamides / chemistry*
  • Aldehydes / chemistry*
  • Aza Compounds / chemistry*
  • Crystallography, X-Ray
  • Cyclization
  • Ketones / chemistry*
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Structure
  • Pyrrolidines / chemical synthesis*
  • Pyrrolidines / chemistry
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry
  • Stereoisomerism

Substances

  • Acetamides
  • Aldehydes
  • Aza Compounds
  • Ketones
  • Pyrrolidines
  • Spiro Compounds