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Chiral salen - Ni (II) based spherical porous silica as platform for asymmetric transfer hydrogenation reaction and synthesis of potent drug intermediate montekulast
Molecular Catalysis ( IF 3.9 ) Pub Date : 2021-01-20 , DOI: 10.1016/j.mcat.2020.111367
Meenakshi Shukla , K.C. Barick , H.G. Salunke , Sudeshna Chandra

Heterogeneous catalyst has an edge over homogeneous systems in terms of recyclability, activity, stability and recovery. Silica has evolved as a good support material in heterogeneous systems due to its stability and ability to get modified as per the end application. Herein, we report a novel chiral Ni-Schiff base derived catalyst and its immobilization into mesoporous silica which was synthesized by post-grafting process. The chiral catalyst demonstrated remarkably high catalytic activity, enantioselectivity (up to 99 % enantiomers excess) for heterogeneous asymmetric transfer hydrogenation of various ketones. The developed catalyst was characterized by Ultraviolet-visible spectroscopy (UV–vis), Fourier-Transform Infrared spectroscopy (FT-IR), X-ray Powder Diffraction (XRD), Brunauer-Emmett-Teller (BET isotherm), Scanning Electron Microscopy – Energy Dispersive X-ray Spectroscopy (SEM-EDX), High Resolution – Transmission Electron Microscopy (HR-TEM), Vibrating Sample Magnetometer (VSM), X-ray Photoelectron Spectroscopy (XPS) and elemental analysis. The catalyst could be recovered and reused for multiple consecutive runs without losing the enantioselectivity. The chiral catalyst was used in asymmetric transfer hydrogenation reaction for synthesizing enantiomerically pure drug intermediate Montekulast.



中文翻译:

手性Salen-Ni(II)基球形多孔二氧化硅为平台,用于不对称转移氢化反应和强效药物中间体孟克司特的合成

就可循环性,活性,稳定性和回收率而言,非均相催化剂在均相系统方面具有优势。二氧化硅由于其稳定性和根据最终应用进行改性的能力,已发展成为异构系统中的良好支撑材料。在本文中,我们报道了一种新型的手性镍席夫碱衍生的催化剂及其固定化到介孔二氧化硅中,该介孔二氧化硅是通过接枝过程合成的。手性催化剂对各种酮的非均相不对称转移氢化显示出极高的催化活性和对映选择性(对映异构体最多可达99%)。所开发的催化剂的特征在于紫外可见光谱(UV-vis),傅立叶变换红外光谱(FT-IR),X射线粉末衍射(XRD),Brunauer-Emmett-Teller(BET等温线),扫描电子显微镜–能量色散X射线能谱(SEM-EDX),高分辨率–透射电子显微镜(HR-TEM),振动样品磁强计(VSM),X射线光电子能谱(XPS)和元素分析。催化剂可被回收并重复用于多个连续运行而不会损失对映选择性。手性催化剂用于不对称转移氢化反应中,以合成对映体纯的药物中间体Monteklast。

更新日期:2021-01-20
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