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
JournalAngewandte Chemie International Edition
Issue number27
Publication statusPublished - 1 Jul 2019

    Research areas

  • alkenes, dichlorination, enantioselectivity, halogenation, organocatalysis

ID: 46830735