Gold Catalysis Enabling Furan-Fused Cyclobutenes as a Platform toward Cross Cycloadditions

The inherently strained furan-fused cyclobutenes, in situ generated via cycloisomerizations of allenyl ketones bearing cyclopropyl moiety under gold catalysis, have been utilized as reactive building blocks toward cross cycloadditions. The [4 + 2] and [3 + 2] annulations of these species with benzo­...

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Bibliographic Details
Published in:Organic letters 2021-05, Vol.23 (9), p.3701-3705
Main Authors: Zhang, Shouzhi, Tang, Aijie, Xie, Ruyu, Zhao, Zhiqiang, Yao, Jinzhong, Miao, Maozhong
Format: Article
Language:English
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Summary:The inherently strained furan-fused cyclobutenes, in situ generated via cycloisomerizations of allenyl ketones bearing cyclopropyl moiety under gold catalysis, have been utilized as reactive building blocks toward cross cycloadditions. The [4 + 2] and [3 + 2] annulations of these species with benzo­[c]­isoxazoles and N-iminoquinazolinium ylides furnish various three-dimensional cyclobutane-bridged polyheterocycles in good yields. A wide range of typically electron-deficient 1,3-dienes, heterodienes, and 1,3-dipoles can trap furan-fused cyclobutenes to afford several polycyclic architectures.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.1c01079