Remarkable [3+2] Annulations of Electron-Rich Olefins with Unstabilized Azomethine Ylides
Remarkable [3+2] Annulations of Electron-Rich Olefins with Unstabilized Azomethine Ylides
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DOI：
10.1055/s-0030-1258026
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发表时间：
2010-10-01
期刊：
影响因子：
2
通讯作者：
Xu, Wenjian
中科院分区：
文献类型：
--
作者：
Davoren, Jennifer E.;Gray, David L.;Xu, Wenjian
在此，我们想传达的是，从商业三甲基胺N-氧化物产生的不稳定的甲亚胺叶立德将以良好的产率与富电子和非极化烯烃进行显着的1，3-偶极环加成。烯烃上的宽范围的取代基是容许的，只要它们与过量的LDA相容。这种新的反应范围的演示应鼓励其他人尝试在具有挑战性的3，4-二取代吡咯烷的合成中作为偶氮甲碱叶立德前体的N-氧化三甲胺。
Herein we would like to communicate that an unstabilized azomethine ylide generated from commercial trimethylamine N-oxide will undergo a remarkable 1,3-dipolar cycloaddition in good yield with electron-rich and unpolarized olefins. A broad range of substituents on the alkenes are tolerated provided they are compatible with excess LDA. This demonstration of novel reaction scope should encourage others to try trimethylamine N-oxide as an azomethine ylide precursor in the synthesis of challenging 3,4-disubstituted pyrrolidines.