Cationic gold- and silver-catalyzed cycloisomerizations of propargylic ureas: A selective entry to oxazolidin-2-imines and imidazolidin-2-ones

Olga P. Pereshivko, Vsevolod A. Peshkov, Jeroen Jacobs, Luc Van Meervelt, Erik V. Van Der Eycken

Research output: Contribution to journalArticlepeer-review

44 Citations (Scopus)

Abstract

A comparative study on transition metal-catalyzed cycloisomerizations of propargylic ureas derived in situ from secondary propargylic amines and tosyl isocyanate was performed. The influence of catalytic system on the reaction outcome was thoroughly studied on two model examples resulting in the establishment of two selective protocols for both O- and N-cyclizations. The application of cationic gold(I) catalysis generally resulted in a formation of oxazolidin-2-imines as major products while the application of silver(I) triflate selectively provided the corresponding imidazolidin-2-ones. An attempt to rationalize the observed chemoselectivity is described. The scope of both processes was demonstrated through the use of variously substituted secondary propargylic amines.

Original languageEnglish
Pages (from-to)781-789
Number of pages9
JournalAdvanced Synthesis and Catalysis
Volume355
Issue number4
DOIs
Publication statusPublished - Mar 11 2013
Externally publishedYes

Keywords

  • chemoselectivity
  • cyclization
  • gold
  • heterocycles
  • silver

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry

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