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Organocatalytic, Enantioselective Dichlorination of Unfunctionalized Alkenes
Author(s) -
Wedek Volker,
Van Lommel Ruben,
Daniliuc Constantin G.,
De Proft Frank,
Hennecke Ulrich
Publication year - 2019
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201901777
Subject(s) - enantioselective synthesis , cinchona , chemistry , electrophile , organic chemistry , nucleophile , chloride , chlorine , combinatorial chemistry , catalysis
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.