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Synthesis 2022; 54(18): 3962-3976
DOI: 10.1055/a-1794-0770
DOI: 10.1055/a-1794-0770
feature
Facile Access to Spiro[4.5]decanes through Oxidative Dearomatization-Induced Ring Expansion of Cyclobutanes
We acknowledge the financial support from the National Natural Science Foundation of China (21971140), the Tsinghua University Spring Breeze Fund (2021Z99CFY015), and the Beijing Natural Science Foundation (M21011).
Abstract
A mechanistically interesting and practical method for the synthesis of functionalized spiro[4.5]decanes is developed, featuring oxidative dearomatization-induced ring expansion of cyclobutanes as the key element. The new method enables facile access to a variety of spiro[4.5]cyclohexadienones with good efficiency and generality. Further elaboration of the resulting products into other valuable scaffolds is also explored, leading to the discovery of an interesting compound that displays a promising biological profile. Moreover, we have also conducted a comprehensive computational study that provides a deep insight into the mechanism of the reaction.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1794-0770.
- Supporting Information
Publication History
Received: 12 February 2022
Accepted after revision: 10 March 2022
Accepted Manuscript online:
10 March 2022
Article published online:
03 May 2022
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For selected examples, see:
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