18913-16-1Relevant academic research and scientific papers
Copper-Catalyzed Formation of α-Alkoxycycloalkenones from N-Tosylhydrazones
Su, Naijing,Theorell, Juliana A.,Wink, Donald J.,Driver, Tom G.
, p. 12942 - 12946 (2015/11/02)
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. 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 reaction proceeds by the cycloaddition of a copper carbenoid with an ester, and a subsequent Lewis acid-catalyzed [1,2] alkyl shift of the in situ generated alkoxyepoxide intermediate.
