Phosphine-catalyzed [3 + 2] annulation of 2-aminoacrylates with allenoates and mechanistic studies
Phosphine-catalyzed [3 + 2] annulation of 2-aminoacrylates with allenoates and mechanistic studies
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DOI：
10.1039/d0cy00092b
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发表时间：
2020-06
影响因子：
5
通讯作者：
Xiao-yun Wu;Hou Gui;Harish Jangra;Yin Wei;H. Zipse;M. Shi
中科院分区：
文献类型：
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作者：
Xiao-yun Wu;Hou Gui;Harish Jangra;Yin Wei;H. Zipse;M. Shi
本发明公开了一种通过膦催化的2-氨基丙烯酸酯与丙二烯酸酯的[3 + 2]缩甲醛环化合成含有氨基季立体中心的3-吡咯啉的方便有效的策略。广泛的底物顺利地进行了这一反应，提供了一系列的3-吡咯啉在良好的至优异的产率，它可以扩展到一个克级反应。利用动力学曲线和计算的甲基阴离子亲和力（MAA）值来解释反应中使用的不同联烯酸盐的反应活性，这为此类反应的催化机制提供了深入的了解。
A convenient and efficient strategy for the synthesis of 3-pyrrolines containing an amino quaternary stereogenic center via phosphine-catalyzed formal [3 + 2] annulation of 2-aminoacrylates with allenoates is disclosed. A wide range of substrates underwent this reaction smoothly, affording a series of 3-pyrrolines in good to excellent yields, and it could be extended to a gram-scale reaction. The kinetic profiles and the calculated methyl anion affinity (MAA) values were employed to explain the reactivities of different allenoates used in the reaction, which provides deep understanding for the catalytic mechanism of this type of reaction.