Synthesis of rigid chiral C3-symmetric triptycene-based ligands and their application in enantioselective Cu(I)-catalyzed aziridination of chalcones

Ilya Kisets, Dmitri Gelman*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

12 Scopus citations

Abstract

The design and synthesis of C3- symmetric or pseudo-C3-symmetric ligands present a particular challenge because the molecular frames available for fitting C3 symmetry are rare. Herein, we report on the synthesis and characterization of new C3-symmetric tripodal TripTOX ligands, based on the rigid triptycene backbone, and on their successful application in the asymmetric copper-catalyzed aziridination reaction. The ligand showed good to excellent performance in the copper-catalyzed asymmetric aziridination of chalcones. The catalyst derived from the new ligand appears to be the catalyst of choice when substrates have a coordinating nature.

Original languageAmerican English
Article number121804
JournalJournal of Organometallic Chemistry
Volume941
DOIs
StatePublished - 7 Jun 2021

Bibliographical note

Publisher Copyright:
© 2021 Elsevier B.V.

Keywords

  • C3-symmetric
  • aziridination
  • copper-catalyzed
  • enantioselective
  • oxazoline
  • triptycene

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