Highly regio- and stereoselective synthesis of α-(N-Alkyl-N-p- toluenesulfonyl)-β-bromo-ketones via Ni(OAc)2-catalyzed aminobromination of chalcones

Hao Sun, San Jun Zhi, Jian Lin Han, Guigen Li, Yi Pan

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

The combinations of N-methyl-p-toluenesulfonamide/NBS and N-ethyl-p-toluenesulfonamide/NBS were found to be good nitrogen/halogen resources for the aminohalogenation of α,β-unsaturated ketones in the presence of Ni(OAc)2 as the catalyst for the synthesis of vicinal haloamino ketone derivatives. The introduction of N-alkyl groups to the nitrogen resources resulted in excellent regio- and stereoselectivity for both electron-donating and electron-withdrawing group-attached unsaturated ketone substrates. The structure of the resulting products has been unambiguously confirmed by X-ray crystal structure analysis.

Original languageEnglish
Pages (from-to)269-276
Number of pages8
JournalChemical Biology and Drug Design
Volume75
Issue number3
DOIs
StatePublished - Mar 2010

Keywords

  • Aminohalogenation
  • Ketones
  • N-alkyl-p-toluenesulfonamide
  • Nickel acetate
  • α,β-unsaturated

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