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Facile Construction of Tetrahydropyrrolizines by Iron-Catalyzed Double Cyclization of Alkene-Tethered Oxime Esters with 1,2-Disubstituted Alkenes.

Takuya ShimbayashiDaiki NakamotoKazuhiro OkamotoKouichi Ohe
Published in: Organic letters (2018)
The iron-catalyzed cycloaddition reaction of alkene-tethered oxime esters with 1,2-disubstituted alkenes afforded tetrahydropyrrolizines, the structural motif often seen in bicyclic alkaloids. The reaction proceeds through consecutive cycloaddition reactions. These include, first, intramolecular cyclization, followed by intermolecular cyclization with a 1,2-disubstituted alkene in a regioselective manner where an imine moiety first generated plays a pivotal role.
Keyphrases
  • room temperature
  • iron deficiency
  • energy transfer
  • quantum dots
  • electron transfer
  • highly efficient
  • ionic liquid
  • metal organic framework
  • visible light