4.6 Article

Selective approach to N-substituted tertiary 2-pyridones

Journal

NEW JOURNAL OF CHEMISTRY
Volume 46, Issue 23, Pages 11138-11142

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/d2nj01065h

Keywords

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Funding

  1. Fundamental Research Funds for Central Universities [1191329135]
  2. Key Laboratory Construction Program of Xi'an Municipal Bureau of Science and Technology [201805056ZD7CG40]
  3. Xi'an Jiao Tong University [7121182002]

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Regio- and enantioselective amination of readily available vinyl cyclic carbonates with ambivalent 2-hydroxypyridines has been achieved using a Pd(0)/DACH-naphthyl catalyst system. The reaction proceeds under simple conditions, providing access to chiral N-substituted 2-pyridones that bear elusive tertiary carbon centers. This catalytic method overcomes a significant drawback previously associated with transition metal-catalyzed allylic substitution procedures.
The regio- and enantioselective amination of readily available vinyl cyclic carbonates with ambivalent 2-hydroxypyridines has been achieved using a Pd(0)/DACH-naphthyl catalyst system. The reaction proceeds under simple conditions, providing access to chiral N-substituted 2-pyridones that bear elusive tertiary carbon centers. A significant drawback previously related to making these products via transition metal-catalyzed allylic substitution procedures is overcome by this catalytic method.

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