Journal
CHINESE CHEMICAL LETTERS
Volume 35, Issue 2, Pages -Publisher
ELSEVIER SCIENCE INC
DOI: 10.1016/j.cclet.2023.109184
Keywords
Anion cascade reactions; 3-Isoquinuclidone; Bridged polycyclic lactams; Bis-Michael addition reaction; Hemiaminalization
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Bridged polycyclic lactams are important structural units in organic functional materials, natural products, and pharmaceuticals. A flexible and efficient anion cascade reaction was developed for the preparation of bridged polycyclic lactams. The reaction showed good yields of various highly substituted bridged polycyclic lactams.
Bridged polycyclic lactams are important structural units in organic functional materials, natural products, and pharmaceuticals. A flexible and efficient anion cascade reaction was developed for the preparation of bridged polycyclic lactams from readily available malonamides and 1,4-dien-3-ones. Various highly substituted bridged polycyclic lactams were synthesized in good to excellent yields by tandem nucleophilic sequences in the presence of tBuOK in commercially available EtOH solvent at 60 degrees C. Notably, the simple reactions can be run on a gram scale. Mechanistically, bis-Michael addition reaction and hemiaminalization reactions are involved in the tandem transformation.(c) 2023 Published by Elsevier B.V. on behalf of Chinese Chemical Society and Institute of Materia Medica, Chinese Academy of Medical Sciences.
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