Asymmetric Cu-Catalyzed 1,4-Dearomatization of Pyridines and Pyridazines without Preactivation of the Heterocycle or Nucleophile
Author(s)
Gribble, Michael William; Guo, Sheng; Buchwald, Stephen Leffler
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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.
Date issued
2018-04Department
Massachusetts Institute of Technology. Department of ChemistryJournal
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
ISSN
1520-5126