Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume -, Issue -, Pages -Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.202302111
Keywords
[6+4] cycloadditions; 10-membered azecines; palladium catalysis; polycyclic compound; transannular reaction
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A catalytic formal [6+4] cycloaddition reaction was developed for the synthesis of 10-membered azecines, which produced benzofuran-fused azecines with high diastereoselectivity in moderate to good yields through the reaction of delta-vinylvalerolactones and benzofuran-derived azadienes under palladium catalysis. The unique transformations involving the transannular reaction of these compounds for the construction of polycyclic compounds were also demonstrated.
Azecine fragments are frequently presented in natural products and bioactive compounds. However, minor efforts have been devoted to these 10-membered N-heterocycles, and their synthesis is still challenging. Reported herein is the first catalytic formal [6+4] cycloaddition for the synthesis of 10-membered azecines. Under palladium catalysis, the reaction of delta-vinylvalerolactones and benzofuran-derived azadienes proceeds smoothly to afford benzofuran-fused azecines with high diastereoselectivity in moderate to good yields. A unique transannular reaction of these 10-membered azecines for the construction of polycyclic compounds is also demonstrated. Catalytic formal [6+4] cycloaddition was developed for the synthesis of 10-membered azecines. Under palladium catalysis, the reaction of delta-vinylvalerolactones and benzofuran-derived azadienes proceeds smoothly to afford benzofuran-fused azecines with high diastereoselectivity in moderate to good yields. The unique transformations involving the transannular reaction of these compounds was also demonstrated.image
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