Stereoselective synthesis of -sulfinylamino isocyanides and 2-imidazolines

Guido V. Janssen, Esther Vicente-García, Wouter Vogel, J. Chris Slootweg, Eelco Ruijter, Koop Lammertsma, Romano V.A. Orru

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)


An efficient asymmetric synthesis of -sulfinylamino isocyanides is reported on the basis of the highly diastereoselective addition of 9-isocyanofluorene to optically pure N-tert-butanesulfinimines. The resulting optically pure isocyanides readily cyclized to give optically pure 2-imidazolines upon removal of the sulfinyl group. Furthermore, the -sulfinylamino isocyanides were used as chiral inputs in Ugi and Passerini multicomponent reactions to generate new types of (pseudo)peptide scaffolds. Optically pure -sulfinylamino isocyanides are synthesized in a highly diastereoselective addition of 9-isocyanofluorene with N-tert-butanesulfinimines. Follow-up chemistry demonstrates that they are excellent precursors for the preparation of optically pure 2-imidazolines. Furthermore, they are applied in Ugi and Passerini multicomponent reactions; TMSOTf = trimethylsilyl trifluoromethanesulfonate, DIPEA = N,N- diisopropylethylamine.

Original languageEnglish
Pages (from-to)3762-3766
Number of pages5
JournalEuropean Journal of Organic Chemistry
Issue number18
Publication statusPublished - Jun 2014
Externally publishedYes


  • Chirality
  • Isocyanides
  • Multicomponent reactions
  • Nitrogen heterocycles
  • Sulfinimines
  • Synthetic methods

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry


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