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Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
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JoVE Journal Chemistry
Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions

DOI:
10.3791/64019-v

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04:38 min

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July 28, 2022

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, , ,
1Department of Energy Science,Sungkyunkwan University, 2Department of Chemistry,Hankuk University of Foreign Studies

Chapters

  • 00:05Introduction
  • 00:45Synthesis of Bisaziridine
  • 02:04Selective Ring-Opening of Non-Activated Aziridines
  • 03:03Results: Characterization Data for the Products
  • 03:53Conclusion

Summary

Automatic Translation

Automatic Translation

Contiguous bisaziridines containing non-activated and activated aziridines were synthesized by asymmetric organocatalytic aziridinations and then subjected to chemoselective ring-opening reactions under acidic or basic conditions. The non-activated aziridine ring opens with less reactive nucleophiles under acidic conditions, whereas the activated aziridine ring opens with more reactive nucleophiles under basic conditions.

Tags

BisaziridineRegioselective Ring-openingNitrogen-rich MoleculesBioactive CompoundsNatural ProductsSodium BorohydrideAldehyde ReductionEthyl AlcoholNMR Characterization

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