Organocatalytic asymmetric intramolecular aza-Henry reaction: facile synthesis of trans-2,3-disubstituted tetrahydroquinolines

Org Biomol Chem. 2015 Jun 28;13(24):6825-31. doi: 10.1039/c5ob00795j.

Abstract

An enantio- and diastereoselective organocatalytic intramolecular aza-Henry (nitro-Mannich) reaction has been developed. The trans-2-aryl-3-nitro-tetrahydroquinoline products are obtained in high yields and in good enantioselectivities with a bifunctional tertiary amine-thiourea catalyst. Excellent enantioselectivities were obtained after single recrystallization of some products.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry
  • Catalysis
  • Crystallization
  • Crystallography, X-Ray
  • Models, Molecular
  • Quinolines / chemical synthesis*
  • Quinolines / chemistry
  • Stereoisomerism
  • Thiourea / chemistry

Substances

  • Amines
  • Quinolines
  • 1,2,3,4-tetrahydroquinoline
  • Thiourea