Practical Synthesis of Chiral N-Heterocyclic Carbene Triazolium Salts Containing a Hydroxy Functional Handle

Vasudevan Dhayalan, Kanchan Mal, Anat Milo

Research output: Contribution to journalArticlepeer-review

3 Scopus citations

Abstract

A library of functionalized chiral pyrrolidine-based N-heterocyclic carbene triazolium salts containing a hydroxy handle is prepared from readily accessible chiral (S)-pyroglutamic acid in eight steps. This improved synthetic protocol affords increased yields for known structures and 18 new NHCs are prepared by this method. The presence of a hydroxy handle offers potential for further functionalization and for non-covalent control over catalytic reactions in which the NHCs can serve as organocatalysts or ligands for organometallic catalysis.

Original languageEnglish
Pages (from-to)2845-2864
Number of pages20
JournalSynthesis
Volume51
Issue number14
DOIs
StatePublished - 1 Jan 2019

Keywords

  • N-heterocyclic carbenes
  • arylhydrazines
  • benzyl alcohol
  • desilylation
  • organocatalysis
  • organomagnesium reagents
  • protecting groups
  • triazolium salts

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