Chemoselective addition of isocyanides to N-tert-butanesulfinimines

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Abstract

The reaction of isocyanides with N-tert-butanesulfinimines shows remarkable chemoselectivity. β-Sulfinylamino isocyanides are formed exclusively with aromatic sulfinimines, while α-sulfeneimino acetamides result when using aliphatic derivatives. A mechanism is suggested for the latter transformation, together with an explanation for the observed selectivity. Finally, a scope study is presented for this remarkably chemoselective reaction.

Original languageEnglish
Pages (from-to)5116-5119
Number of pages4
JournalOrganic letters
Volume16
Issue number19
Early online date17 Sep 2014
DOIs
Publication statusPublished - 3 Oct 2014

Keywords

  • Acetamides/chemical synthesis
  • Catalysis
  • Cyanides/chemistry
  • Imines/chemical synthesis
  • Molecular Structure
  • Stereoisomerism
  • Sulfonium Compounds/chemical synthesis

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