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Readily available phenol-derived biaryls reacted with allenes under palladium catalysis to provide a variety of highly valuable spiro[cyclohexane-1,1'-indene]-2,5-dien-4-ones. This new catalytic process, involving a key step of regioselective allylative dearomatization… Click to show full abstract
Readily available phenol-derived biaryls reacted with allenes under palladium catalysis to provide a variety of highly valuable spiro[cyclohexane-1,1'-indene]-2,5-dien-4-ones. This new catalytic process, involving a key step of regioselective allylative dearomatization of phenol, proceeded efficiently through a [3 + 2] spiroannulation pathway by overcoming undesired β-hydride elimination. Preliminary asymmetric studies showed that high enantioselectivity could be realized by using a commercially available PHOX ligand. Moreover, the potential application of this method was exemplified by several further transformations.
Journal Title: Organic letters
Year Published: 2018
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