Palladium-Catalyzed Ring-Opening of 2-Alkylidenecyclobutanols: Stereoselective Synthesis of γ,δ-Unsaturated Ketones by C−C Bond Cleavage
| Autor: | Jian Cao, Zhan-Jiang Zheng, Yu-Li Sun, Yu-Ming Cui, Ling Chen, Zheng Xu, Feng-Na Sun, Li-Wen Xu |
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| Rok vydání: | 2017 |
| Předmět: |
chemistry.chemical_classification
Double bond 010405 organic chemistry Stereochemistry Aryl chemistry.chemical_element General Chemistry 010402 general chemistry Ring (chemistry) 01 natural sciences Medicinal chemistry 0104 chemical sciences Catalysis chemistry.chemical_compound chemistry Functional group Stereoselectivity Bond cleavage Palladium |
| Zdroj: | Advanced Synthesis & Catalysis. 360:411-415 |
| ISSN: | 1615-4150 |
| DOI: | 10.1002/adsc.201701078 |
| Popis: | A facile synthesis of γ,δ-unsaturated ketones via palladium-catalyzed ring-opening of 2-alkylidenecyclobutanols with organic halides is described. The key step involves Csp3-Csp2 bond cleavage via palladium-catalyzed β-carbon elimination. The desired γ,δ-unsaturated ketones are obtained in good to excellent yields and broad functional group tolerability. Aryl, heteroaryl, benzyl, and alkynyl halides all readily participate to forge tri-substituted carbon-carbon double bond in a stereoselective manner. |
| Databáze: | OpenAIRE |
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