Organocatalytic, Enantioselective Dichlorination of Unfunctionalized Alkenes

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

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18 Citaten (Scopus)

Samenvatting

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.

Originele taal-2English
Pagina's (van-tot)9239-9243
Aantal pagina's5
TijdschriftAngewandte Chemie International Edition
Volume58
Nummer van het tijdschrift27
DOI's
StatusPublished - 1 jul 2019

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