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Direct Synthesis of Chiral Porphyrin Macrocyclic Receptors via Regioselective Nitration.

Shaji VargheseBram SpierenburgAnne SwartjesPaul B WhitePaul TinnemansJohannes A A W ElemansRoeland J M Nolte
Published in: Organic letters (2018)
Nitration of tetraphenylporphyrin cage compound 1, at -40 °C, leads to the regioselective formation of the chiral mononitro compound 2 (75% isolated yield) and, at -30 °C, to the achiral syn-dinitro-derivative 3 and the chiral anti-dinitro derivative 4 in a diastereomeric ratio of 5:2, which were separated by chromatography (46 and 20% yields, respectively). The structures of the compounds were confirmed by X-ray crystallography.
Keyphrases
  • capillary electrophoresis
  • mass spectrometry
  • ionic liquid
  • high resolution
  • photodynamic therapy
  • high speed
  • liquid chromatography
  • water soluble
  • magnetic resonance imaging
  • ms ms
  • solid phase extraction