Regio- and stereoselective copper-catalyzed synthesis of vicinal haloamino ketones from α,β-unsaturated ketones

Dianjun Chen, Cody Timmons, Steven Chao, Guigen Li

Research output: Contribution to journalArticle

62 Scopus citations

Abstract

The regio- and stereoselective aminochlorination of α,β- unsaturated ketones has been developed. The reaction was conducted with N,N-dichloro-p-toluenesulfonamide (4-TsNCl2) as the nitrogen/halogen source and CuOTf as the catalyst, at 0 °C to room temperature. This method provides an easy access to vicinal haloamino ketones, with excellent regioselectivity and up to quantitative yields. Both aromatic and aliphatic enones react well with 4-TsNCl2 under the present system, but give opposite regioselectivity.

Original languageEnglish
Pages (from-to)3097-3101
Number of pages5
JournalEuropean Journal of Organic Chemistry
Issue number14
DOIs
StatePublished - Jul 12 2004

Keywords

  • Aminohalogenation
  • Haloamines
  • α,β-Unsaturated ketones

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