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- Title
Skeletal Rearrangement of O-Propargylic Formaldoximes by a Gold-Catalyzed Cyclization/Intermolecular Methylene Transfer Sequence.
- Authors
Nakamura, Itaru; Gima, Shinya; Kudo, Yu; Terada, Masahiro
- Abstract
Skeletal rearrangement of O-propargylic formaldoximes, in the presence of gold catalysts, afforded 4-methylene-2-isoxazolines in good to excellent yields by an intermolecular methylene transfer. In addition, the cascade reaction with maleimide in the presence of a gold catalyst afforded isoxazole derivatives by cyclization/methylene transfer and a subsequent ene reaction, whereas that using a copper catalyst gave oxazepines through a 2,3-rearrangement.
- Subjects
REARRANGEMENTS (Chemistry); GOLD catalysts; RING formation (Chemistry); INTERMOLECULAR interactions; OXIMES; BOND transfer
- Publication
Angewandte Chemie International Edition, 2015, Vol 54, Issue 24, p7154
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201501856