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Towards an Asymmetric Organocatalytic α-Azidation of β-Ketoesters.

Maximilian TiffnerLotte StockhammerJohannes SchörgenhumerKatharina RöserMario Waser
Published in: Molecules (Basel, Switzerland) (2018)
Detailed investigations concerning the organocatalytic (asymmetric) α-azidation of prochiral β-ketoesters were carried out. It was shown that the racemic version of such a reaction can either be carried out under oxidative conditions using TMSN₃ as the azide-source with quaternary ammonium iodides as the catalysts, or by using hypervalent iodine-based electrophilic azide-transfer reagents with different organocatalysts. In addition, the latter strategy could also be carried out with modest enantioselectivities when using simple cinchona alkaloid catalysts, albeit with relatively low yields.
Keyphrases
  • highly efficient
  • transition metal
  • solid state
  • metal organic framework
  • psychometric properties
  • ionic liquid