Pd‐Catalyzed Enantioselective Ring Opening/Cross‐Coupling and Cyclopropanation of Cyclobutanones
| Autor: | Ke-Fang Yang, Feng-Na Sun, Yu-Li Sun, Li-Wen Xu, Kezhi Jiang, Ling Chen, Jian Cao, Zheng Xu |
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| Rok vydání: | 2019 |
| Předmět: |
Nucleophilic addition
010405 organic chemistry Cyclopropanation Chemistry Aryl Enantioselective synthesis General Chemistry 010402 general chemistry Ring (chemistry) 01 natural sciences Combinatorial chemistry Catalysis 0104 chemical sciences Stereocenter chemistry.chemical_compound Intramolecular force |
| Zdroj: | Angewandte Chemie International Edition. 58:897-901 |
| ISSN: | 1521-3773 1433-7851 |
| DOI: | 10.1002/anie.201813071 |
| Popis: | A palladium-catalyzed enantioselective sequential ring-opening/cross-coupling of cyclobutanones is disclosed that provides chiral indanones bearing C3-quaternary stereocenters. The reaction process involves palladium-catalyzed nucleophilic addition of cyclobutanones and aryl halides, enantioselective β-carbon elimination, and intermolecular trapping of a transient σ-alkylpalladium complex with boronic acids. Alternatively, an intramolecular cyclopropanation is realized through C-H bond functionalization in the absence of external coupling reagents, affording chiral cyclopropane-fused-indanones in good yields and enantioselectivity. |
| Databáze: | OpenAIRE |
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