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Enzyme-Inspired Assembly: Incorporating Multivariate Interactions to Optimize the Host–Guest Configuration for High-Speed Enantioselective Catalysis
ACS Applied Materials & Interfaces ( IF 8.3 ) Pub Date : 2020-09-25 , DOI: 10.1021/acsami.0c13802 Dan Deng 1 , Qinghao Meng 1 , Zhangnan Li 1 , Rongchen Ma 1 , Yajie Yang 1 , Zeyu Wang 1 , Ning Zhang 1 , Xiaoqin Zou 1 , Guangshan Zhu 1 , Ye Yuan 1
ACS Applied Materials & Interfaces ( IF 8.3 ) Pub Date : 2020-09-25 , DOI: 10.1021/acsami.0c13802 Dan Deng 1 , Qinghao Meng 1 , Zhangnan Li 1 , Rongchen Ma 1 , Yajie Yang 1 , Zeyu Wang 1 , Ning Zhang 1 , Xiaoqin Zou 1 , Guangshan Zhu 1 , Ye Yuan 1
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To achieve a rapid asymmetry conversion, the substrate objects suffer from accelerated kinetic velocity and random rotation at the cost of selectivity. Inspired by natural enzymes, optimizing the host–guest configuration will realize the high-performance enantioselective conversion of chemical reactions. Herein, multivariate binding interactions were introduced into the 1D channel of a chiral catalyst to simulate the enzymatic action. An imidazolium group was used to electrophilically activate the C═O unit of a ketone substrate, and the counterion binds the hydrogen donor isopropanol. This binding effect around the catalytic center produces strong stereo-induction, resulting in high conversion (99.5% yield) and enantioselectivity (99.5% ee) for the asymmetric hydrogenation of biomass-derived acetophenone. In addition, the turnover frequency of the resulting catalyst (5160 h–1 TOF) is more than 58 times that of a homogeneous Ru-TsDPEN catalyst (88 h–1 TOF) under the same condition, which corresponds to the best performance reported till date among all existing catalysts for the considered reaction.
中文翻译：
受酶启发的组装：整合多元相互作用以优化用于高速对映选择性催化的宿主-客体配置
为了实现快速的不对称转换，衬底物体遭受了加速的动力学速度和随机旋转，而代价是选择性。受天然酶的启发，优化宿主-客体的配置将实现化学反应的高性能对映选择性转化。在此，将多元结合相互作用引入手性催化剂的1D通道中以模拟酶促作用。咪唑鎓基团用于亲电活化酮底物的C = O单元，而抗衡离子则结合氢供体异丙醇。催化中心周围的这种结合作用产生了强烈的立体感应，导致生物质衍生的苯乙酮的不对称氢化反应具有很高的转化率（99.5％收率）和对映选择性（99.5％ee）。此外，–1 TOF）是相同条件下均相Ru-TsDPEN催化剂（88 h –1 TOF）的58倍以上，相当于迄今为止所考虑的所有现有催化剂中报告的最佳性能。
更新日期：2020-10-21
中文翻译：
受酶启发的组装：整合多元相互作用以优化用于高速对映选择性催化的宿主-客体配置
为了实现快速的不对称转换，衬底物体遭受了加速的动力学速度和随机旋转，而代价是选择性。受天然酶的启发，优化宿主-客体的配置将实现化学反应的高性能对映选择性转化。在此，将多元结合相互作用引入手性催化剂的1D通道中以模拟酶促作用。咪唑鎓基团用于亲电活化酮底物的C = O单元，而抗衡离子则结合氢供体异丙醇。催化中心周围的这种结合作用产生了强烈的立体感应，导致生物质衍生的苯乙酮的不对称氢化反应具有很高的转化率（99.5％收率）和对映选择性（99.5％ee）。此外，–1 TOF）是相同条件下均相Ru-TsDPEN催化剂（88 h –1 TOF）的58倍以上，相当于迄今为止所考虑的所有现有催化剂中报告的最佳性能。
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