Asymmetric Intramolecular Conjugate Addition Nitro-Mannich Route to cis-2-Aryl-3-nitrotetrahydroquinolines

Org Lett. 2015 Aug 21;17(16):4090-3. doi: 10.1021/acs.orglett.5b02036. Epub 2015 Aug 13.

Abstract

Reductive cyclization of 2-iminonitrostyrenes (from the condensation of 2-aminostyrenes with an aldehyde and subsequent nitration of the alkene) using a bifunctional thiourea catalyst and tert-butyl-Hantzsch ester leads to an intramolecular conjugate hydride addition nitro-Mannich reaction to give the corresponding cis-2-aryl-3-nitrotetrahydroquinolines as single diastereoisomers in high yields and enantioselectivities.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Cyclization
  • Esters
  • Molecular Structure
  • Nitro Compounds / chemical synthesis*
  • Nitro Compounds / chemistry
  • Quinolines / chemical synthesis*
  • Quinolines / chemistry
  • Stereoisomerism
  • Styrenes / chemistry
  • Thiourea / chemistry

Substances

  • Esters
  • Nitro Compounds
  • Quinolines
  • Styrenes
  • 1,2,3,4-tetrahydroquinoline
  • Thiourea