Asymmetric Cu-Catalyzed 1,4-Dearomatization of Pyridines and Pyridazines without Preactivation of the Heterocycle or Nucleophile
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Accepted version
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Author(s)
Gribble, Michael William
Guo, Sheng
Buchwald, Stephen Leffler
Date Issued
April 2018
Journal
Journal of the American Chemical Society
Publisher
American Chemical Society (ACS)
Citation
Gribble, Michael W., Jr., Sheng Guo, and Stephen L. Buchwald. "Asymmetric Cu-Catalyzed 1,4-Dearomatization of Pyridines and Pyridazines without Preactivation of the Heterocycle or Nucleophile." Journal of the American Chemical Society 140, 15 (Apr. 2018): p. 5057-60 doi 10.1021/JACS.8B02568 ©2018 Author(s)
Version
Author's final manuscript
Abstract
We show that a chiral copper hydride (CuH) complex catalyzes C-C bond-forming dearomatization of pyridines and pyridazines at room temperature. The catalytic reaction operates directly on free heterocycles and generates the nucleophiles in situ, eliminating the need for stoichiometric preactivation of either reaction partner; further, it is one of very few methods available for the enantioselective 1,4-dearomatization of heteroarenes. Combining the dearomatization with facile derivatization steps enables one-pot syntheses of enantioenriched pyridines and piperidines.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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DOI of Published Version
https://doi.org/10.1021/JACS.8B02568
