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- Title
Pd‐Catalyzed Enantioselective Ring Opening/Cross‐Coupling and Cyclopropanation of Cyclobutanones.
- Authors
Cao, Jian; Chen, Ling; Sun, Feng‐Na; Sun, Yu‐Li; Jiang, Ke‐Zhi; Yang, Ke‐Fang; Xu, Zheng; Xu, Li‐Wen
- Abstract
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.
- Subjects
PALLADIUM catalysts; RING-opening reactions; COUPLING reactions (Chemistry); CYCLOPROPANATION; CYCLOBUTANONES
- Publication
Angewandte Chemie, 2019, Vol 131, Issue 3, p907
- ISSN
0044-8249
- Publication type
Article
- DOI
10.1002/ange.201813071