Diastereodivergent Synthesis of Bromoiminolactones: Electrochemical and Chemical Bromoiminolactonization of α-Allylmalonamides
Diastereodivergent Synthesis of Bromoiminolactones: Electrochemical and Chemical Bromoiminolactonization of α-Allylmalonamides
复制标题
溴亚氨基内酯的非对映异构合成：α-烯丙基丙二酰胺的电化学和化学溴亚氨基内酯化
DOI：
10.1055/s-0037-1611791
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发表时间：
2019
期刊：
影响因子：
2
通讯作者：
Onomura Osamu
中科院分区：
文献类型：
--
作者：
Yamamoto Kosuke;Ishimaru Keiko;Mizuta Satoshi;Minato Daishirou;Kuriyama Masami;Onomura Osamu
本文报道了由α-取代α-烯丙基丙二酰胺经溴代亚氨基内酯化合成N-取代亚氨基内酯的非对映异构体。而在常规化学条件下溴环化提供cis-溴亚胺内酯，电化学条件下表现出互补的非对映选择性，得到的反式产品。在这两组条件下，氮原子和丙二酰胺的α-位上的各种取代基都是容许的，从而以优异的产率和高的非对映选择性得到相应的亚氨基内酯。
A diastereodivergent synthesis of N-substituted iminolactones by bromoiminolactonization of α-substituted α-allylmalonamides is reported. Whereas bromocyclization under conventional chemical conditions providedcis-bromoiminolactones, electrochemical conditions exhibited complementary diastereoselectivity to afford thetrans-products. A variety of substituents on the nitrogen atoms and an α-position of the malonamide were tolerated under both sets of conditions to afford the corresponding iminolactones in excellent yields and high diastereoselectivities.