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Organocatalytic, Enantioselective Dichlorination of Unfunctionalized Alkenes

Tijdschriftbijdrage - Tijdschriftartikel

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.

Tijdschrift: Angewandte Chemie - International Edition
ISSN: 1433-7851
Issue: 27
Volume: 58
Pagina's: 9239-9243
Jaar van publicatie:2019
Trefwoorden:alkenes, dichlorination, enantioselectivity, halogenation, organocatalysis
CSS-citation score:2
Toegankelijkheid:Open