Synthesis and Evaluation of Novel Planar-Chiral Monophosphine Ligands Bearing Ferrocene-Triazole Backbones
Synthesis and Evaluation of Novel Planar-Chiral Monophosphine Ligands Bearing Ferrocene-Triazole Backbones
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带有二茂铁-三唑主链的新型平面手性单膦配体的合成与评价
DOI：
10.1002/ejic.202100967
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发表时间：
2022
影响因子：
2.3
通讯作者：
Fukuzawa
中科院分区：
文献类型：
--
作者：
Suguru;Sakai; Kazuya Kanemoto; Shin-ichi;Fukuzawa
我们制备了新型的平面手性单膦配体，其具有二茂铁-三唑骨架。这些配体通过一系列步骤产生，包括通过非对映选择性叠氮化和（S）-Ugi胺的Huisgen环加成合成三唑，然后甲基化和膦引入。由于Huisgen环加成反应的底物范围较广，该方法适用于各种类似物的制备。这些配体在Suzuki-Miyaura偶联反应中表现出良好的催化活性，特别是那些涉及大体积底物的反应。此外，这些配体的光学活性版本中使用的不对称Suzuki-Miyaura偶联反应，以产生具有中等的对映选择性的轴向手性联萘化合物。本研究开发的配体是第一个可用于不对称反应的三唑型联芳基单膦配体，有望成为获得手性化合物的新工具。
We prepared novel planar chiral monophosphine ligands bearing ferrocene‐triazole backbones. These ligands were produced in a series of steps that included triazole synthesis by diastereoselective azidation and Huisgen cycloaddition of (S)‐Ugi's amine, followed by methylation and phosphine introduction. This method was applicable to the preparation of various analogues due to the wide substrate scope of the Huisgen cycloaddition reaction. These ligands showed good catalytic activity in Suzuki–Miyaura coupling reactions, especially those involving bulky substrates. Furthermore, the optically active versions of these ligands were used in the asymmetric Suzuki–Miyaura coupling reaction to produce the axial chiral binaphthyl compound with moderate enantioselectivity. The ligand developed in this study is the first triazole‐type biaryl‐ monophosphine ligand that can be used in asymmetric reactions, and it is expected to be a new tool for the accessing chiral compounds.