Catalytic intermolecular aldol reactions of transient amide enolates in domino Michael/aldol reactions of nitroalkanes, acrylamides, and aldehydes
Catalytic intermolecular aldol reactions of transient amide enolates in domino Michael/aldol reactions of nitroalkanes, acrylamides, and aldehydes
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DOI：
10.1039/d0gc04111d
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发表时间：
2021-02
期刊：
影响因子：
9.8
通讯作者：
Shunya Morita;T. Yoshimura;J. Matsuo
中科院分区：
文献类型：
--
作者：
Shunya Morita;T. Yoshimura;J. Matsuo
使用催化量的 KOH 在 DMSO 中进行硝基烷烃、丙烯酰胺和醛的三组分反应，得到 β'-羟基-γ-硝基酰胺。机理研究表明该反应是通过多米诺迈克尔/羟醛反应进行的。通过迈克尔将硝基阴离子与DMSO中的丙烯酰胺加成而形成的瞬时酰胺烯醇化物的高度亲核性质使得能够在酸性硝基烷存在下实现酰胺烯醇化物的催化分子间羟醛反应。
Three-component reactions of nitroalkanes, acrylamides, and aldehydes by using a catalytic amount of KOH in DMSO gave β′-hydroxy-γ-nitro amides. Mechanistic studies suggested that the reactions proceeded by domino Michael/aldol reactions. The highly nucleophilic nature of transient amide enolates that were formed by Michael addition of nitronate anions to acrylamides in DMSO enabled the realization of catalytic intermolecular aldol reactions of amide enolates in the presence of acidic nitroalkanes.