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Updated: May 15, 2025

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Published on: July 28, 2022
Palladium-Catalyzed Enantioselective Ring-Opening/Cyanation of Cyclobutanones
Gang Wang1, Jie Yang1, Ming Chen1
1Key Laboratory of Synthetic and Nature Molecule Chemistry of Ministry of Education, Department of Chemistry & Materials Science, Northwest University, Xi'an 710127, China.
Abstract:
Palladium-catalyzed asymmetric transformations involving cyanide anions remain a challenge due to the strong affinity between cyanide anions and palladium, which induces alterations in the coordination sphere of the palladium center. Herein, palladium-catalyzed enantioselective cyanation is achieved via a ring-opening/cross-coupling process between aryl halide-tethered cyclobutanones and Zn(CN)2. This reaction is demonstrated to exhibit broad substrate scope and robust enantioselectivity. The synthetic utility is highlighted by converting the product into amide, carboxylic acid, and ester without racemization.
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