Facile Access to Spiro[4.5]decanes through Oxidative Dearomatization-Induced Ring Expansion of Cyclobutanes

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.

Key words

oxidative dearomatization - phenol - cyclobutane - ring expansion - spiro[4.5]decane

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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