Catalytic Asymmetric Synthesis of Tertiary Alkyl Fluorides: Negishi Cross-Couplings of Racemic α,α-Dihaloketones
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Liang-2014-Catalytic asymmetric.pdf
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Author(s)
Liang, Yufan
Fu, Gregory C.
Date Issued
March 2014
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Liang, Yufan, and Gregory C. Fu. “Catalytic Asymmetric Synthesis of Tertiary Alkyl Fluorides: Negishi Cross-Couplings of Racemic Α,α-Dihaloketones.” Journal of the American Chemical Society 136, no. 14 (April 9, 2014): 5520–5524. © 2014 American Chemical Society
Version
Final published version
Abstract
The 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.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/ja501815p
