Copper‐Catalyzed Formation of α‐Alkoxycycloalkenones from N‐Tosylhydrazones. Issue 44 (7th September 2015)

• Record Type: Journal Article
• Authors: Su, Naijing; Theorell, Juliana A.; Wink, Donald J.; Driver, Tom G.
• Is Part Of: Angewandte Chemie international edition. Volume 54:Issue 44(2015)
• Page Start: 12942
• Page End: 12946
• Publication Date: 2015-09-07
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201505993
• Languages: English
• ISSNs: 1433-7851

Abstract

<abstract abstract-type="main" xml:lang="en"> <title>Abstract</title> <p>The combination of 20 mol % of copper iodide and lithium <italic>tert</italic>‐butoxide triggers the formation of a broad range of substituted, functionalized α‐alkoxy 2<italic>H</italic>‐naphthalenones from readily available <italic>N</italic>‐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.</p> </abstract>