ja501815p_si_004.cif (22.31 kB)
Catalytic Asymmetric Synthesis of Tertiary Alkyl Fluorides: Negishi Cross-Couplings of Racemic α,α-Dihaloketones
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posted on 2015-12-17, 01:31 authored by Yufan Liang, Gregory C. FuThe
development of new approaches to the construction of fluorine-containing
target molecules is important for a variety of scientific disciplines,
including medicinal chemistry. In this Article, we describe a method
for the catalytic enantioselective synthesis of tertiary alkyl fluorides
through Negishi reactions of racemic α-halo-α-fluoroketones,
which represents the first catalytic asymmetric cross-coupling that
employs geminal dihalides as electrophiles. Thus, selective reaction
of a C–Br (or C–Cl) bond in the presence of a C–F
bond can be achieved with the aid of a nickel/bis(oxazoline) catalyst.
The products of the stereoconvergent cross-couplings, enantioenriched
tertiary α-fluoroketones, can be converted into an array of
interesting organofluorine compounds.
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electrophilepresenceDihaloketonesTheRacemicgeminal dihalidesenantioenrichedarrayNegishi reactionsdisciplinevarietyTertiary Alkyl FluoridesracemicArticleenantioselective synthesisapproachmethodCatalytic Asymmetric Synthesisstereoconvergentfluoroketonemoleculeconstructioncatalystalkyl fluorideshaloorganofluorine compoundsaidbond
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