Nickel/Bis(oxazoline)-Catalyzed Asymmetric Kumada Reactions of Alkyl Electrophiles: Cross-Couplings of Racemic alpha-Bromoketones
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Author(s)
Lou, Sha
Fu, Gregory C.
Alternative Title
Nickel/Bis(oxazoline)-Catalyzed Asymmetric Kumada Reactions of Alkyl Electrophiles: Cross-Couplings of Racemic α-Bromoketones
Date Issued
February 2010
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society
Citation
Lou, Sha, and Gregory C. Fu. “Nickel/Bis(oxazoline)-Catalyzed Asymmetric Kumada Reactions of Alkyl Electrophiles: Cross-Couplings of Racemic alpha-Bromoketones.” Journal of the American Chemical Society 132.4 (2010): 1264-1266.
Version
Author's final manuscript
Abstract
The first asymmetric Kumada reactions of alkyl electrophiles are described, specifically, cross-couplings of racemic α-bromoketones with aryl Grignard reagents. Several features of this investigation are of interest. First, the couplings proceed at remarkably low temperature (−40 or −60 °C), which enables the asymmetric synthesis of racemization-prone alpha-arylketones. Second, dialkyl ketones undergo enantioselective coupling in good ee and yield. Third, readily available bis(oxazolines) are shown for the first time to be effective ligands for cross-couplings of alkyl electrophiles, thereby opening the door to new opportunities in asymmetric catalysis.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/ja909689t
