Padwa Albert, Boonsombat Jutatip, Rashatasakhon Paitoon, Willis Jerremey
Department of Chemistry, Emory University, Atlanta, GA 30322, USA.
Org Lett. 2005 Aug 18;7(17):3725-7. doi: 10.1021/ol0513589.
The rhodium(II)-catalyzed cyclization/cycloaddition cascade of a o-carbomethoxyaryl diazo dione is described as a potential route to the oxatricyclo[6.3.1.0(0,0)]dodecane substructure of the icetexane diterpene komaroviquinone. The initially formed carbonyl ylide dipole prefers to cyclize to an epoxide at 25 degrees C but can be induced to undergo cycloaddition across the tethered pi-bond at higher temperatures. [reaction: see text]
据描述，铑（II）催化的邻甲氧基羰基芳基重氮二酮的环化/环加成串联反应是合成icetexane二萜komaroviquinone的氧杂三环[6.3.1.0(0,0)]十二烷亚结构的一条潜在途径。最初形成的羰基叶立德偶极子在25℃时倾向于环化为环氧化物，但在较高温度下可被诱导穿过连接的π键进行环加成。[反应：见正文]
