Stereoselective Mannich reaction catalyzed by tetrahydroindolo[3,2-b]indole under solvent-free conditions
作者:Jing Shi、Li-Zhu Zhang、Yong Pan、Deng-Qiang Feng、Guang-Yu Wu、Ke Yang、Xiao-Qiang Sun、Zheng-Yi Li
DOI:10.1016/j.tetlet.2022.154128
日期:2022.10
have been designed and synthesized for the three-component direct Mannich reaction of aromatic aldehydes and aromatic amines with ketones. Significantly, the organocatalyst 2a delivered excellent catalytic stereoselectivity (up to >99:1) with good yields (up to 88 %) for above reaction process under the solvent-freeconditions at room temperature. X-ray diffraction analysis reveals that organocatalyst
一系列基于吲哚的有机催化剂(4b,9b-aryl-4b,5,9b,10-tetrahydroindolo[3,2- b ]indole 衍生物)(2a-2f)已被设计和合成用于三组分直接曼尼希芳香醛和芳香胺与酮的反应。值得注意的是,有机催化剂2a在室温和无溶剂条件下为上述反应过程提供了优异的催化立体选择性(高达 >99:1)和良好的收率(高达 88%)。X 射线衍射分析表明,有机催化剂2a具有八元中心环结构,具有有趣的应变四环连接性。2a中包含的特征刚性V形吲哚环结构并且2a和中间体之间形成的氢键相互作用优于抗立体选择性产物。
Catalytic Asymmetric Synthesis of Inherently Chiral Saddle‐Shaped Dibenzo[b,f][1,5]diazocines†
作者:Jinmiao Zhou、Mengyao Tang、Xiaoyu Yang
DOI:10.1002/cjoc.202400243
日期:2024.9
Dibenzo[b,f][1,5]diazocines are a class of eight-membered heterocycles, which exhibit unique rigid saddle-shaped structure and possess inherent chirality. In this study, we report a convenient and straightforward method for the catalytic enantioselective synthesis of these unique chiral molecules through chiral phosphoric acid-catalyzed dimerization of 2-acylbenzoisocyanates. Notably, the addition
二苯并[ b , f ][1,5]二氮杂辛是一类八元杂环化合物,具有独特的刚性鞍状结构并具有固有的手性。在这项研究中,我们报告了一种方便、直接的方法,通过手性磷酸催化 2-酰基苯并异氰酸酯的二聚,催化对映选择性合成这些独特的手性分子。值得注意的是,添加相应的2-酰基苯胺作为助催化剂显着提高了这些反应的效率,并且简单的相分离操作导致产物具有优异的对映体纯度。进行实验研究是为了阐明这些反应背后的机制,并根据研究结果提出合理的反应机制。