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Organocatalytic Synthesis of Benzazetidines by Trapping Hemiaminals with Protecting Groups.

Riccardo SalvioSimone PlacidiArianna SinibaldiAntonio Di SabatoDario C BuscemiAndrea RossiAchille AntenucciAndrei V MalkovMarco Bella
Published in: The Journal of organic chemistry (2019)
Benzazetidines are highly strained and inherently unstable heterocycles. There are only few methodologies for assembling these compounds. Here, a protocol is presented to trap an elusive cyclic, four-membered hemiaminal structure. This method affords several benzazetidines in moderate to good yields (up to 81%), and it uses inexpensive materials and does not require catalysts based on transition metals. The high ring strain energy of these benzazetidine systems was estimated by density functional theory calculations to be about 32 kcal mol-1. This synthesis can be applied also on gram scale with reaction yield essentially unchanged.
Keyphrases
  • density functional theory
  • molecular dynamics
  • randomized controlled trial
  • gram negative
  • highly efficient
  • health risk
  • climate change
  • multidrug resistant