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pH-Controlled Chirality Inversion in Enantiodifferentiating Photocyclodimerization of 2-Antharacenecarboxylic Acid Mediated by γ-Cyclodextrin Derivatives.

Kuppusamy KanagarajWenting LiangMing RaoJiabin YaoWuanhua WuGuo ChengJiecheng JiXueqin WeiChao PengCheng Yang
Published in: Organic letters (2020)
Several γ-cyclodextrin (γ-CDx) derivatives were used as chiral hosts for the photocyclodimerization of 2-anthracenecarboxylic acid (AC). The effect of pH on photoreactivity and stereochemical outcome of photoproducts was investigated. Upon changing the solution pH, the stereochemical outcome of HH cyclodimer 3 was inverted from 25.2% to -64.4% and 41.2% to -76.2%, respectively, in the photocyclodimerization of AC mediated by bis-quinoline-modified γ-CDx 7 and its N-methylated derivative 8.
Keyphrases
  • ionic liquid
  • capillary electrophoresis
  • molecular docking
  • magnetic resonance imaging
  • magnetic resonance
  • computed tomography
  • contrast enhanced
  • single molecule
  • water soluble