Organocatalytic, Enantioselective Dichlorination of Unfunctionalized Alkenes.

Authors :: Wedek V
Van Lommel R
Daniliuc CG
De Proft F
Hennecke U
Source :: Angewandte Chemie (International ed. in English) [Angew Chem Int Ed Engl] 2019 Jul 01; Vol. 58 (27), pp. 9239-9243. Date of Electronic Publication: 2019 May 27.
Publication Year :: 2019
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.<br /> (© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)