Article
Chemistry, Organic
Bram B. C. Peters, Norman Birke, Luca Massaro, Pher G. Andersson
Summary: The catalytic asymmetric hydrogenation of olefins is a powerful method for synthesizing chiral compounds. By using an iridium N,P-complex catalyst, various prochiral unsaturated amides can be efficiently reduced with high enantioselectivities. The attractive features of this method include its application in the synthesis of fenpropidin and the potential use of isomeric mixtures as starting materials.
Article
Chemistry, Multidisciplinary
Wei Zhao, Wenji Wang, Huan Zhou, Qishan Liu, Zhiqing Ma, Haizhou Huang, Mingxin Chang
Summary: A one-pot asymmetric hydrogenation of pyridines with subsequent N-alkylation using a traceless Bronsted acid activation strategy is reported. The reaction exhibits high stereoselectivity and can be used to synthesize indolizidines and quinolizidines. Experimental and theoretical studies reveal that chloride anion and noncovalent interactions play important roles in determining the stereoselectivity of the reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Zhengyu Han, Gang Liu, Xuanliang Yang, Xiu-Qin Dong, Xumu Zhang
Summary: The study developed an efficient and simple synthetic strategy for obtaining both enantiomers of chiral tetrahydroquinoline derivatives through the adjustment of reaction solvents. Gram-scale asymmetric hydrogenation proceeded well with low-catalyst loading, and a possible reaction process was revealed based on various experiments conducted.
Article
Chemistry, Multidisciplinary
Haibo Wu, Hao Su, Erik J. Schulze, Bram B. C. Peters, Mark D. Nolan, Jianping Yang, Thishana Singh, Marten S. G. Ahlquist, Pher G. Andersson
Summary: The study presents a highly efficient desymmetrization of 1,4-dienes through iridium-catalyzed site- and enantioselective hydrogenation, allowing the installation of two adjacent stereogenic centers. High yields and excellent selectivities were achieved for a range of substrates, and the methodology was demonstrated by synthesizing key intermediates of natural products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Biochemistry & Molecular Biology
Bo Xu, Xiaotian Shi, Xiang Liu, Hua Cao
Summary: This review summarizes the research progress in the synthesis of chiral cyclic compounds by photocatalytic cycloaddition reaction in the past 5 years, and expounds the reaction conditions, characters, and corresponding proposed mechanism, providing guidance for the development of this field.
Article
Chemistry, Multidisciplinary
Zhaofeng Gao, Jingwen Liu, Haizhou Huang, Huiling Geng, Mingxin Chang
Summary: The research reports on efforts to merge two asymmetric reductive amination reactions into a single-step transformation, utilizing specific catalyst and acid additives to successfully synthesize enantiopure secondary amine products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Si-Yong Yin, Qiansujia Zhou, Chen-Xu Liu, Qing Gu, Shu-Li You
Summary: The iridium-catalyzed asymmetric C-H alkylation was used for the first time to construct N-N biaryl atropisomers. The method showed good yields (up to 98%) and excellent enantioselectivity (up to 99% ee) for the synthesis of axially chiral molecules based on indole-pyrrole skeleton. This method also allowed the synthesis of N-N bispyrrole atropisomers with high yields and enantioselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Organic
Dezheng Xie, Ziyi Chen, Chun-Jiang Wang, Xiu-Qin Dong
Summary: Phosphonates and derivatives with an α-chiral center are important compounds found in natural products, pharmaceuticals, and agrochemicals. The synthesis of these compounds has been the focus of recent research, with advancements in asymmetric catalysis such as hydrogenation, addition reactions, and nucleophilic additions to α,β-unsaturated phosphonates. The continuous development of enantioselective catalytic methods and the future applications of these compounds are also discussed.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Organic
Lei He, Bram B. C. Peters, Xu Quan, Shaohu Zhao, Tianrui Huang, Shuting Ren, Pher G. Andersson, Taigang Zhou
Summary: This article describes a method for synthesizing highly enantioselective alpha-chiral amine compounds using NHC, P-iridium complexes catalyzed asymmetric hydrogenation of imines. The hydrogenation proceeds smoothly, even under hydrogen pressure. Experimental results indicate that the reduction process most likely progresses through a combination of direct hydrogenation and a hydrogen transfer process using either H-2 or iPrOH as the reductant, respectively.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Organic
Sudipta Ponra, Bernard Boudet, Phannarath Phansavath, Virginie Ratovelomanana-Vidal
Summary: This review summarizes the recent work on the catalytic asymmetric hydrogenation of prochiral olefins, focusing on the development of new catalytic systems and the extension of these asymmetric reductions to new classes of enamides.
SYNTHESIS-STUTTGART
(2021)
Review
Chemistry, Multidisciplinary
Johannes Grosskopf, Thorsten Bach
Summary: Upon irradiation with a suitable chiral catalyst, racemic compounds can be converted into enantiopure compounds through a process called photochemical deracemization. This review comprehensively covers the research and current developments in this field, discussing the reactions and mechanistic details underlying the presented reaction. Photochemical deracemization offers a unique opportunity to directly obtain enantiopure compounds from racemates, and short-lived intermediates play a key role in determining the enantioselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Biochemistry & Molecular Biology
Amanda L. Kwan, Robert H. Morris
Summary: This article introduces the largest-scale asymmetric catalytic process for the industrial production of (S)-metolachlor, which is achieved through the hydrogenation of N-(2-ethyl-6-methylphenyl)-1-methoxypropan-2-imine. The authors propose a plausible proton-first, outer-sphere mechanism based on density functional theory calculations that explains the reduction of the sterically hindered bond in the imine.
Article
Chemistry, Organic
Tushar Janardan Pawar, Liliette Barcelona-Cazanave, Israel Bonilla-Landa, Magdalena Escobar, J. Oscar C. Jimenez-Halla, Alma Altuzar-Molina, Patricia Romero-Arellano, Andrew J. F. Edmunds, Martin Aluja, Jose Luis Olivares-Romero
Summary: This study presents a highly efficient iridium-catalyzed asymmetric hydrogenation approach for the total synthesis of biologically active (R,L) A. ludens host marking pheromone (HMP). The use of a novel Ir(i)-complex and a chiral P,N-ligand resulted in excellent enantioselectivities of up to 94% ee. The streamlined synthetic route involving seven reaction steps offers improved efficiency and shorter synthesis timelines compared to previous methods.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Guanghao Huang, Regis Guillot, Cyrille Kouklovsky, Boris Maryasin, Aurelien de la Torre
Summary: A broadly applicable diastereo- and enantioselective inverse-electron-demand Diels-Alder reaction of 2-pyrones and acyclic enol ethers is reported, leading to the synthesis of bridged bicyclic lactones with high yields and enantioselectivities using a copper(II)-BOX catalytic system. Mechanistic studies suggest a stepwise mechanism, and the synthetic potential of the bridged bicyclic lactones is demonstrated through the enantioselective synthesis of polyfunctional cyclohexenes and cyclohexadienes, as well as a carbasugar unit.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Qinglin Zhang, Kang Liang, Chang Guo
Summary: A novel electrolytic system has been introduced to divert standard ionic reactivity, providing a brand-new pattern of reactivity-electricity-driven asymmetric catalysis, which serves as a privileged chiral platform for enantioselective radical allylation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Haizhou Huang, Xiaoyan Liu, Le Zhou, Mingxin Chang, Xumu Zhang
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2016)
Article
Chemistry, Organic
Haizhou Huang, Yunfei Zhao, Yang Yang, Le Zhou, Mingxin Chang
Article
Chemistry, Organic
Haizhou Huang, Zitong Wu, Guorui Gao, Le Zhou, Mingxin Chang
ORGANIC CHEMISTRY FRONTIERS
(2017)
Article
Chemistry, Applied
Xin Zheng, Bonan Cao, Tang-lin Liu, Xumu Zhang
ADVANCED SYNTHESIS & CATALYSIS
(2013)
Article
Chemistry, Multidisciplinary
Tang-Lin Liu, Chun-Jiang Wang, Xumu Zhang
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2013)
Article
Chemistry, Multidisciplinary
Mingxin Chang, Yuhua Huang, Shaodong Liu, Yonggang Chen, Shane W. Krska, Ian W. Davies, Xumu Zhang
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2014)
Article
Chemistry, Organic
Huan Zhou, Wenlei Zhao, Tao Zhang, Haodong Guo, Haizhou Huang, Mingxin Chang
SYNTHESIS-STUTTGART
(2019)
Article
Multidisciplinary Sciences
Shuai Yuan, Guorui Gao, Lili Wang, Cungang Liu, Lei Wan, Haizhou Huang, Huiling Geng, Mingxin Chang
NATURE COMMUNICATIONS
(2020)
Article
Chemistry, Multidisciplinary
Zhaofeng Gao, Jingwen Liu, Haizhou Huang, Huiling Geng, Mingxin Chang
Summary: The research reports on efforts to merge two asymmetric reductive amination reactions into a single-step transformation, utilizing specific catalyst and acid additives to successfully synthesize enantiopure secondary amine products.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Rongrong Xie, Cungang Liu, Renwei Lin, Runchen Zhang, Haizhou Huang, Mingxin Chang
Summary: The strong coordination between 1,2-diamines and transition metals can hinder or disrupt regular catalytic cycles. In this study, we employed sets of additives to ensure a smooth transformation catalyzed by rhodium complexes and versatile phosphoramidite-phosphine ligands. The tunability of the ligands was fully utilized to accommodate various diamines and alpha-ketoesters for the efficient synthesis of chiral 3,4-dihydroquinox-alinones.
Article
Multidisciplinary Sciences
Zitong Wu, Wenji Wang, Haodong Guo, Guorui Gao, Haizhou Huang, Mingxin Chang
Summary: Direct asymmetric reductive amination is an efficient method for obtaining chiral amines. In this study, the authors demonstrate how primary alkyl amines can undergo this transformation in the presence of an iridium catalyst with sterically tuneable chiral phosphoramidite ligands, leading to the synthesis of pharmaceutical compounds.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Rongrong Xie, Huan Zhou, Hui Lu, Yawei Mu, Gong Xu, Mingxin Chang
Summary: An efficient enantioselective reductive amination and amidation cascade reaction has been developed using iridium or rhodium complexes as catalysts. The coupling of simple alkyl diamines and alpha-ketoesters, assisted by sets of additives, smoothly leads to chiral cyclic piperazinone products. The reaction proceeds through distinctive types of intermediates for disubstituted and monosubstituted alkyl diamine substrates, and achieves high enantioselectivity with different transition metals, iridium for the former and rhodium for the latter.
Article
Chemistry, Multidisciplinary
Jing Wang, Wenji Wang, Xiongyu Yang, Jingwen Liu, Haizhou Huang, Mingxin Chang
Summary: In this study, a practical homogeneous direct reductive amination (DRA) procedure using iridium catalysis was reported. The reaction conditions were mild and additive-free, allowing for the formation of structurally and functionally diverse amine products, including drugs and compounds from late-stage manipulation. DFT studies revealed that the reaction proceeds via an outer-sphere H-addition pathway with important roles played by pi-pi interactions and H-bonding.
SCIENCE CHINA-CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Zitong Wu, Shaozhi Du, Guorui Gao, Wenkun Yang, Xiongyu Yang, Haizhou Huang, Mingxin Chang
Article
Chemistry, Multidisciplinary
Huan Zhou, Yuan Liu, Suhua Yang, Le Zhou, Mingxin Chang
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2017)
