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
