Reactive intermediates from DMDO oxidation of ynamides. Trapping of a de novo chiral push-pull carbene via cyclopropanation
Reactive intermediates from DMDO oxidation of ynamides. Trapping of a de novo chiral push-pull carbene via cyclopropanation
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DOI：
10.1021/ol703083k
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发表时间：
2008-02-21
期刊：
影响因子：
5.2
通讯作者：
Hsung, Richard P.
中科院分区：
文献类型：
--
作者：
Al-Rashid, Ziyad F.;Hsung, Richard P.
描述了亚胺类化合物的DMDO氧化反应轮廓。这项工作说明了第一个例子，高度非对映选择性的分子内环丙烷化的推拉式卡宾派生的炔氧化。此外，亚硝胺的氧化提供了对酮亚胺的便捷途径，并揭示了对电子偏置环氧烯化学的机械洞察。
The reaction profile of DMDO oxidations of ynamides; is described. This work illustrates the first examples of highly diastereoselective intramolecular cyclopropanations of a push-pull carbene derived from alkyne oxidation. In addition, the ynamide oxidation provides facile access to ketoimides and reveals mechanistic insights into the chemistry of electronically biased oxirenes.