Manganese (IV) oxide-catalyzed electrophilic diamination of electron-deficient alkenes provides an easy synthesis of α,β-diamino acid and ketone derivatives for peptidomimetic studies

C. Timmons, L. M. Mcpherson, D. Chen, H. X. Wei, G. Li

Research output: Contribution to journalArticle

13 Scopus citations

Abstract

Manganese (IV) oxide was found to catalyze the diamination reaction of α,β-unsaturated esters and ketones with N,N-dichloro-p- toluenesulfonamide and acetonitrile as the halogen and nitrogen sources. The reaction is convenient to be conducted by simply mixing three reactants in the presence of manganese dioxide catalyst and 4 Å molecular sieves, and provides an easy access to 1-p-toluenesulfonyl-3-trichloromethyl-4,5-imidazoline derivatives, which are useful building blocks for peptidomimetic studies.

Original languageEnglish
Pages (from-to)249-254
Number of pages6
JournalJournal of Peptide Research
Volume66
Issue number5
DOIs
StatePublished - Nov 2005

Keywords

  • Alkene addition
  • Diamine
  • Diamino acid
  • Imidazoline
  • Manganese (IV) oxide

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