Selenolactams as Synthetic Intermediates for the Synthesis of Polycyclic Amines via Seleno-Claisen Rearrangements
Selenolactams as Synthetic Intermediates for the Synthesis of Polycyclic Amines via Seleno-Claisen Rearrangements
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硒代内酰胺作为通过硒代-克莱森重排合成多环胺的合成中间体
DOI：
10.1021/acs.joc.8b00306
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发表时间：
2018
期刊：
影响因子：
--
通讯作者：
Murai Toshiaki
中科院分区：
文献类型：
--
作者：
Shibahara Fumitoshi;Suzuki Masafumi;Kubota Saki;Fukunaga Tomoki;Udagawa Taro;Murai Toshiaki
报道了烯丙基卤与硒代内酰胺的高度非对映选择性α-烯丙基化反应。DFT分析和实验观察表明，该反应是通过aSe烯丙基化的烯硒烯醇的内酰胺，然后由硒-克莱森重排。由此获得的产品可以有效地转化为多环胺使用先前开发的顺序添加的有机金属试剂和闭环复分解。
A highly diastereoselective α-allylation of selenolactams with allyl halides is reported. DFT analyses and experimental observations suggested that this reaction proceeds via aSe-allylation of the eneselenolates of the lactams followed by a seleno-Claisen rearrangement. The thus-obtained products could be efficiently transformed into polycyclic amines using a previously developed sequential addition of organometallic reagents and ring-closing metathesis.