Organocatalytic, Enantioselective Dichlorination of Unfunctionalized Alkenes

Volker Wedek, Ruben Van Lommel, Constantin G. Daniliuc, Frank De Proft, Ulrich Hennecke

Research output: Contribution to journalArticle

18 Citations (Scopus)

Abstract

The use of a new class of unsymmetrical cinchona-alkaloid-based, phthalazine-bridged organocatalysts enabled the highly enantioselective dichlorination of unfunctionalized alkenes. In combination with the electrophilic chlorinating agent 1,3-dichloro-5,5-dimethylhydantoin (DCDMH) and triethylsilyl chloride (TES-Cl) as the source of nucleophilic chloride, 1-aryl-2-alkyl alkenes were dichlorinated with enantioselectivities of up to 94:6 er. Initial mechanistic investigations suggest that no free chlorine is formed, and by replacement of the chloride by fluoride, enantioselective chlorofluorinations of alkenes are possible.

Original languageEnglish
Pages (from-to)9239-9243
Number of pages5
JournalAngewandte Chemie International Edition
Volume58
Issue number27
DOIs
Publication statusPublished - 1 Jul 2019

Keywords

  • alkenes
  • dichlorination
  • enantioselectivity
  • halogenation
  • organocatalysis

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