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- Title
Copper-Catalyzed Formation of α-Alkoxycycloalkenones from N-Tosylhydrazones.
- Authors
Su, Naijing; Theorell, Juliana A.; Wink, Donald J.; Driver, Tom G.
- Abstract
The combination of 20 mol % of copper iodide and lithium tert-butoxide triggers the formation of a broad range of substituted, functionalized α-alkoxy 2 H-naphthalenones from readily available N-tosylhydrazones. The data suggests that this transformation occurs through cycloaddition of a copper carbenoid with an ester, followed by a Lewis acid-catalyzed [1,2] alkyl shift of the in situ generated alkoxyepoxide intermediate.
- Subjects
COPPER catalysts; HYDRAZONES; CARBENE synthesis; CYCLOALKENONES; SUBSTITUENTS (Chemistry); RING formation (Chemistry)
- Publication
Angewandte Chemie International Edition, 2015, Vol 54, Issue 44, p12942
- ISSN
1433-7851
- Publication type
Article
- DOI
10.1002/anie.201505993