Copper Catalyzed [3+2] Annulation Reaction of Exocyclic Sulfonyl Enamides for the Synthesis of N,O‐Spiroketal and Spiroketal

A copper‐catalyzed [3+2] annulation reaction of exocyclic enamines/enol ethers with 1,4‐benzoquinone esters has been developed, providing facile access to N,O‐spiroketals and spiroketals under mild conditions with broad substrate scope (26 examples, 71–94 % yields). Gram scale synthesis and chemical...

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Bibliographic Details
Published in:Chemistry : a European journal 2024-08, Vol.30 (44), p.e202401062-n/a
Main Authors: Cheng, Wen‐Fu, Gao, Shan‐Zeng, Yang, Yu‐Chen, Wang, Lijia
Format: Article
Language:English
Subjects:
3+2
Annulation
Benzoquinone
Chemical reactions
Chemical synthesis
Chiral N,O-spiroketal
Copper
copper catalysis
Esters
Ethers
Exocyclic sulfonyl enamides
Natural products
Organic chemistry
Recrystallization
Substrates
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Summary:A copper‐catalyzed [3+2] annulation reaction of exocyclic enamines/enol ethers with 1,4‐benzoquinone esters has been developed, providing facile access to N,O‐spiroketals and spiroketals under mild conditions with broad substrate scope (26 examples, 71–94 % yields). Gram scale synthesis and chemical transformations demonstrated that this method is potentially useful in the synthesis of natural products and drugs containing a N,O‐ spiroketal moiety. The chiral N,O‐spiroketal could be obtained with 98 % ee after recrystallization, when a chiral SaBOX ligand was employed. A copper‐catalyzed [3+2] annulation reaction of exocyclic enamines with 1,4‐benzoquinone esters has been developed, providing facile access to various N,O‐spiroketals and spiroketals.
ISSN:0947-6539
1521-3765
DOI:10.1002/chem.202401062