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Synthesis of Planar Chiral 2-Aryl Aroylferrocenes via Palladium-Catalyzed C-C Bond-Cleavage/Ring-Opening Reaction. 2021
Hefei National Laboratory for Physical Sciences at the Microscale, and Department of Chemistry, University of Science and Technology of China, Hefei, Anhui 230026, P.R. China.
A palladium-catalyzed ring-opening reaction of optically active ferrocenyl tertiary alcohols for the construction of planar chiral ketones is reported. The stereochemistry of the hydroxyl group in ferrocenyl alcohols markedly affects reaction: ferrocenyl alcohols with a β-hydroxyl group show better reactivity and chemoselectivity than the corresponding α-hydroxyl analogues. The treatment of α-hydroxyl substrates with trifluoroacetic acid successfully realizes the inversion of the orientation of hydroxyl group to the corresponding β-analogues.
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