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Pd(0)-Catalyzed Intermolecular Dearomatizing [3 + 2] Spiroannulation of Phenol-Based Biaryls and Allenes
Wenjie Hu1, Hui Wang1, Lu Bai1
1Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education, College of Chemistry & Materials Science, Northwest University , Xi'an 710127, China.
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.
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