4.8 Article

Palladium-Catalyzed Asymmetric Cascade Intramolecular Cyclization/Intermolecular Michael Addition Reaction of Allenyl Benzoxazinones with 1-Azadienes

Journal

ORGANIC LETTERS
Volume 24, Issue 51, Pages 9442-9446

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.2c03842

Keywords

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Funding

  1. National Natural Science Foundation of China [21801180, 22101156]
  2. Natural Science Foundation of Shandong Province [ZR2018LB010, ZR2022QB083, ZR2021QB032]
  3. Academic promotion programme of Shandong First Medical University [2019QL008]
  4. Incubation Program of Youth Innovation of Shandong Province

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Nitrogen-containing heterocycles play crucial roles in biologically active natural products and pharmaceuticals, and the palladium-catalyzed decarboxylative cycloaddition reactions are powerful synthetic tools. Vinyl benzoxazinones have emerged as versatile building blocks for nitrogenous skeletons.
Nitrogen-containing heterocycles are pivotal scaffolds in various biologically active natural products and pharmaceuticals and exhibit broad biological and medicinal activity.1 The strategies to access N-heterocyclic compounds have drawn great attention; among them, palladium-catalyzed decarboxylative cycloaddition reactions are powerful synthetic tool.2 Recently, vinyl benzoxazinones have emerged as versatile blocks for constructing nitrogenous skeletons.3,4 As shown in Scheme 1, in the presence of a palladium catalyst, vinyl benzoxazinone leads to a pi-allyl Pd-intermediate bearing a Nnucleophile, and the zwitterion could undergo four paths (a- d) to form N-heterocycles. Path a is well developed, and

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