Synthesis 2022; 54(18): 3962-3976
DOI: 10.1055/a-1794-0770
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Facile Access to Spiro[4.5]decanes through Oxidative Dearomatization-Induced Ring Expansion of Cyclobutanes

Shuang Xi
,
Jingyang Zhang
,
Zhen Guo
,
Yumeng Zu
,
Yang Liu
,
Gelin Wang
,

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



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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