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Stereoselective Oxidative Cyclization of N-Allyl Benzamides to Oxaz(ol)ines.

Ayham H AbazidTom-Niklas HollwedelBoris J Nachtsheim
Published in: Organic letters (2021)
This study presents an enantioselective oxidative cyclization of N-allyl carboxamides via a chiral triazole-substituted iodoarene catalyst. The method allows the synthesis of highly enantioenriched oxazolines and oxazines, with yields of up to 94% and enantioselectivities of up to 98% ee. Quaternary stereocenters can be constructed and, besides N-allyl amides, the corresponding thioamides and imideamides are well tolerated as substrates, giving rise to a plethora of chiral 5-membered N-heterocycles. By applying a multitude of further functionalizations, we finally demonstrate the high value of the observed chiral heterocycles as strategic intermediates for the synthesis of other enantioenriched target structures.
Keyphrases
  • ionic liquid
  • capillary electrophoresis
  • high resolution
  • wastewater treatment
  • room temperature
  • mass spectrometry
  • molecular docking