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Recent progress in copper catalyzed asymmetric henry reaction

Chinese Chemical Letters 2018年第6期29卷 873-883页

作者： Sheng Zhang Yanan Li Youguo Xu Zhiyong Wang Hefei National Laboratory for Physical Sciences at Microscale CAS Key Laboratory of Soft Matter Chemistry & Collaborative Innovation Center of SuzhouNano Science and Technology Department of Chemistry University of Science and Technology of China College of Chemistry and Pharmaceutical Engineering Nanyang Normal University

henry reaction is one of the most classical reactions to construct synthetically useful product nitro alcohol, which as a privileged skeleton is widely distributed in various pharmaceuticals. This review summarizes the recent progress of copper-catalyzed asymmetric henry reaction from 2011 to 2016. The significant progress that has been made in this area will be highlighted and some of challenges that the author believes may be hindering further progress will be revealed.

关键词： henry reaction Asymmetric catalysis Copper catalysis Nitro compounds C-C bond formation

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Mn(OAc)_2/Schiff base as a new efficient catalyst system for the henry reaction of nitroalkanes with aldehydes

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Chinese Chemical Letters 2012年第6期23卷 690-694页

作者： Guang Peng Zhou Yong Hai Hui Ning Ning Wan Qiu Ju Liu Zheng Feng Xie Ji De Wang Key Laboratory of Oil and Gas Fine Chemicals Ministry of Education and Xinjiang Uyghur Autonomous RegionCollege of Chemistry and Chemical Engineering Xinfiang University Urumqi 830046 China

A series of novel Schiff bases bearing triazole structure were synthesized and characterized by LR and NMR. Mn（OAc）2/Schiff base efficiently catalyzed henry reaction of nitroalkanes with aldehydes to produce the corresponding products of ^-nitroalcohols, under mild conditions with high yields （up to 99%）. A reaction mechanism is proposed based on the experimental results.

关键词： Schiff base henry reaction Aldehydes Nitroalkanes

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Two Coordination Compounds Bearing Bis（2-dimethylaminoethyl） Ether： Syntheses, Crystal Structures and Catalytic Application to the henry reaction

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Chemical Research in Chinese Universities 2018年第3期34卷 358-362页

作者： LIU Chao LIU Yijie ZHANG Lili JIANG Kun ZHANG Li School of Chemistry and Chemical Engineering Suzhou UniversRy Suzhou 234000 P. R. China

Two novel coordination compounds, namely [Cu2（BDMAEE）（CH3COO）4],,（1） and [Ni（BDMAEE）Cl2]（2） [BDMAEE=bis（2-dimethylaminoethyl） ether], have been synthesized and characterized by IR, elemental analysis, PXRD and X-ray single crystal diffraction. In compound 1, the central Cu（Ⅱ） ion is coordinated with four oxygen atoms and one nitrogen atom, forming a distorted square pyramidal geometry. The asymmetric units composed of one Cu（Ⅱ） ion, two acetates and a half of BDMAEE are connected to form an infinite 1D chain structure by the bridging acetate and the BDMAEE. In compound 2, the central Ni（Ⅱ） ion is coordinated with one oxygen atom, two chlorine anions and two nitrogen atoms, forming a distorted square pyramidal geometry. The compounds exhibited excellent catalytic properties in the henry reaction of nitromethane with some aromatic aldehydes, and the optimized reaction conditions were obtained.

关键词： Copper compound Nickel compound Crystal structure henry reaction

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The study on the application of a new class of chiral 1,4-dimine catalysts to the catalytic asymmetric henry reaction in water

The study on the application of a new class of chiral 1,4-di...

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中国化学会第九届全国有机化学学术会议

作者： Miao-Xi Liu Peng Liu Department of Chemistry School of Pharmacy Fourth Military Medical University

Chiral diamine ligand is one of the most important ligands in asymmetric catalytic *** them,the majority is about 1,2-diamine[1]and about 1,4-diamine[2]is rarely seen *** henry reactions have been extensively studied since 1992[3],However,there is a relatively small number of successful studies for the asymmetric henry reactions in water[4].We have develop a new class of chiral 1,4-dimine thiourea catalysts bearing two 1,4-dioxane and a structure of cinchona alkaloids and it was applied in catalytic asymmetric *** a preliminary screening conditions,we get good yields and up to 78%ee of 5mol%catalyst at low temperature（-30℃）in *** our delighted,the reaction system is no-sensitive to moisture,it also obtain good yields and enantioselectivities（up to 75%ee）in toluene/H2O as a co-solvents or in the saturated brine,especially in water,it can also works *** investigation of the new catalyst is ongoing in our laboratory.

关键词： asymmetric catalytic 1 4-dimine henry reaction in water

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C1-Symmetry diamine catalyzed enantioselective henry reactions

C1-Symmetry diamine catalyzed enantioselective Henry Reactio...

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中国化学会第六届全国分子手性学术研讨会

作者： Yirong Zhou Dengfu Lu Yuefa Gong College of Chemistry and Chemical Engineering Huazhong University of Science and Technology

This work focused on the design and synthesis of C-symmetry diamine catalysts with strong asymmetric induction from commercially available cheap chiral starting materials such as natural amino acids and camphor via several steps of general and practical organic synthetic operations and their applications in catalytic asymmetric henry reactions to access some useful chemical compounds ultimately.

关键词： chiral diamine henry reaction enantioselective

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First total synthesis of eudistalbin A

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Chinese Chemical Letters 2010年第8期21卷 889-891页

作者： Pu Yong Zhang Jun Lei Wang Sheng Biao Wan Tao Jiang School of Medicine and Pharmacy Key Laboratory of Marine DrugsMinistry of Education Ocean University of ChinaQingdao 266003China

Eudistalbin A was isolated from marine tunicate eudistoma album and possess cytotoxic activity（ED_（50）3.2μg/mL） in vitro against the growth of KB human buccal carinoma *** synthetic eudistalbin A showed potent inhibitory activity against the breast carcinoma cell line MDA-231 with an IC_（50） value of 2.1μmol/L using the metabolic assay *** structures of new compounds were confirmed by ~1H NMR,^（13）C NMR,HRMS and optical rotation.

关键词： β-Carboline Eudistalbin A Pictet-Spengler reaction henry reaction Total synthesis

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