Copper‐Catalyzed Formation of α‐Alkoxycycloalkenones from
<i>N</i>
‐Tosylhydrazones
作者:Naijing Su、Juliana A. Theorell、Donald J. Wink、Tom G. Driver
DOI:10.1002/anie.201505993
日期:2015.10.26
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
20 mol%的碘化亚铜和叔丁醇锂的组合会触发从很容易获得的N-甲苯磺酰azo生成大量取代的,官能化的α-烷氧基2 H-萘烯酮。数据表明,这种转变是通过类铜环铜与酯的环加成反应发生的,然后是路易斯酸催化的原位生成的烷氧基环氧中间体的[1,2]烷基转移。