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Organocatalytic, Enantioselective Dichlorination of Unfunctionalized Alkenes. / Wedek, Volker; Van Lommel, Ruben; Daniliuc, Constantin G.; De Proft, Frank; Hennecke, Ulrich.

In: Angewandte Chemie International Edition, Vol. 58, No. 27, 01.07.2019, p. 9239-9243.

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Harvard

Wedek, V, Van Lommel, R, Daniliuc, CG, De Proft, F & Hennecke, U 2019, 'Organocatalytic, Enantioselective Dichlorination of Unfunctionalized Alkenes', Angewandte Chemie International Edition, vol. 58, no. 27, pp. 9239-9243. https://doi.org/10.1002/anie.201901777

APA

Vancouver

Author

Wedek, Volker ; Van Lommel, Ruben ; Daniliuc, Constantin G. ; De Proft, Frank ; Hennecke, Ulrich. / Organocatalytic, Enantioselective Dichlorination of Unfunctionalized Alkenes. In: Angewandte Chemie International Edition. 2019 ; Vol. 58, No. 27. pp. 9239-9243.

BibTeX

@article{2f18ed2cda8445bbafef401b1114c4d0,
title = "Organocatalytic, Enantioselective Dichlorination of Unfunctionalized Alkenes",
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.",
keywords = "alkenes, dichlorination, enantioselectivity, halogenation, organocatalysis",
author = "Volker Wedek and {Van Lommel}, Ruben and Daniliuc, {Constantin G.} and {De Proft}, Frank and Ulrich Hennecke",
year = "2019",
month = "7",
day = "1",
doi = "10.1002/anie.201901777",
language = "English",
volume = "58",
pages = "9239--9243",
journal = "Angewandte Chemie International Edition",
issn = "1433-7851",
publisher = "John Wiley and Sons Ltd",
number = "27",

}

RIS

TY - JOUR

T1 - Organocatalytic, Enantioselective Dichlorination of Unfunctionalized Alkenes

AU - Wedek, Volker

AU - Van Lommel, Ruben

AU - Daniliuc, Constantin G.

AU - De Proft, Frank

AU - Hennecke, Ulrich

PY - 2019/7/1

Y1 - 2019/7/1

N2 - 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.

AB - 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.

KW - alkenes

KW - dichlorination

KW - enantioselectivity

KW - halogenation

KW - organocatalysis

U2 - 10.1002/anie.201901777

DO - 10.1002/anie.201901777

M3 - Article

VL - 58

SP - 9239

EP - 9243

JO - Angewandte Chemie International Edition

JF - Angewandte Chemie International Edition

SN - 1433-7851

IS - 27

ER -

ID: 46830735