Chemoselective addition of isocyanides to N-tert-butanesulfinimines

Guido V. Janssen, Elwin Janssen, Christophe M.L. Vande Velde, Andreas W. Ehlers, J. Chris Slootweg, Eelco Ruijter, Koop Lammertsma, Romano V.A. Orru

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)


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
Issue number19
Publication statusPublished - 3 Oct 2014
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry


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