Copper‐Catalyzed Formation of α‐Alkoxycycloalkenones from N‐Tosylhydrazones |
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| Authors: | Naijing Su Juliana A Theorell Prof?Dr Donald J Wink Prof?Dr Tom G Driver |
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| Institution: | Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, IL 60607 (USA) http://www2.chem.uic.edu/driver |
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| 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 2H‐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. |
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| Keywords: | carbenes copper cyclizations hydrazones synthetic methods |
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