Article
Chemistry, Organic
Congcong Yin, Yingmin Pan, Longsheng Zheng, Bijin Lin, Jialin Wen, Xumu Zhang
Summary: Enantioselective hydrogenation of imines via an outer-sphere mechanism was achieved using an iridium tridentate catalyst, resulting in high enantioselectivities and turnover numbers up to 10,000. This method was successfully applied in the synthesis of chiral amines with an alpha-stereocenter, allowing for the preparation of cinacalcet with remarkably high enantioselectivity.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Zhi Yang, Yu Chen, Linxi Wan, Yuxiao Li, Dan Chen, Jianlin Tao, Pei Tang, Fen-Er Chen
Summary: A highly enantioselective method for the complete hydrogenation of pyrimidinium salts using Ir/(S,S)-f-Binaphane complex as the catalyst was developed. This method provides easy access to fully saturated chiral hexahydropyrimidines, which are prevalent in many bioactive molecules. The reactions exhibit high yields and enantioselectivities under mild reaction conditions without additives. Successful application of this methodology in a continuous flow fashion further extends its practical utility.
Article
Chemistry, Multidisciplinary
Lu Qian, Xixia Tang, Yulei Wang, Guixia Liu, Zheng Huang
Summary: The use of a chiral (NCP)Ir complex as the precatalyst allows for the asymmetric transfer hydrogenation of diaryl ketones. This method is applicable to various ortho-substituted diaryl ketones and can be conducted in gram scale under mild reaction conditions.
CHINESE JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Applied
Yin-Feng Ma, Chuan-Jin Hou, De-Quan Wei, Xinwei He, Ting-Ting Chu, Xiu-shuai Chen, Xiang-Ping Hu
Summary: The asymmetric hydrogenation of beta-ketophosphonates with chiral Ir/P,N,N-ligands catalyst leads to high yields of beta-hydroxyphosphonates with good or excellent enantioselectivities under mild conditions.
APPLIED ORGANOMETALLIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Xue-Song Gu, Ying Xiong, Fan Yang, Na Yu, Pu-Cha Yan, Jian-Hua Xie, Qi-Lin Zhou
Summary: An iridium-catalyzed asymmetric hydrogenation method involving dynamic kinetic resolution was successfully developed using chiral spiro PNN-ligands containing a C5-substituted chiral oxazoline unit. This protocol, combined with simple dehydration, provides a straightforward approach to prepare enantiomerically enriched 3-aryloxy tetrahydrofurans, which are prevalent structural motifs in many approved drugs and clinical candidates.
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)
Article
Chemistry, Physical
Huimin Qi, Lixian Wang, Qiangsheng Sun, Wei Sun
Summary: This article describes a stable iridium catalyst with a chiral 2-pyridyl imidazoline ligand for the asymmetric transfer hydrogenation (ATH) of quinolines and N-heteroaryl compounds. The ATH system uses formic acid as the hydrogen source and water as the solvent. Various quinolines and N-heteroaryl compounds can be efficiently converted into desired products with moderate to good enantioselectivity at a catalyst loading as low as 0.001 mol% under mild conditions.
MOLECULAR CATALYSIS
(2022)
Article
Chemistry, Organic
Jun Yan, Yu Nie, Feng Gao, Qianjia Yuan, Fang Xie, Wanbin Zhang
Summary: An efficient synthesis of chiral 3-arylindanones was achieved through iridium-catalyzed asymmetric hydrogenation, showing good compatibility with various functional groups and delivering high yields with good enantioselectivities. The reaction was performed on a gram-scale with quantitative yield and the products were easily derivatized into natural products and pharmaceutical agents.
Article
Chemistry, Multidisciplinary
Pep Rojo, Medea Molinari, Albert Cabre, Clara Garcia-Mateos, Antoni Riera, Xavier Verdaguer
Summary: Chiral compounds containing nitrogen heteroatoms are crucial for the chemical, pharmaceutical, and agrochemical industries. In this study, a series of P-stereogenic phosphinooxazoline iridium catalysts were synthesized and successfully used in the asymmetric hydrogenation of N-Boc-2,3-diarylallyl amines, achieving high enantioselectivity. The synthetic utility of the obtained 2,3-diarylpropyl amines was also demonstrated.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Multidisciplinary Sciences
Shan Wang, Jian-Xin Zhang, Tian-Yi Zhang, Huan Meng, Bi-Hong Chen, Wei Shu
Summary: Chiral aliphatic amine and alcohol derivatives are difficult to access due to the challenge to differentiate between spatially and electronically similar alkyl groups. By utilizing a nickel-catalyzed enantioselective hydroalkylation, enantioenriched alpha-branched aliphatic acyl amines and esters can be efficiently synthesized with good yields and excellent enantioselectivity.
NATURE COMMUNICATIONS
(2021)
Review
Chemistry, Multidisciplinary
Heng Wang, Jialin Wen, Xumu Zhang
Summary: Asymmetric hydrogenation of double bonds is an effective method for preparing chiral molecules, with noble metals and bidentate ligands showing remarkable reactivity. The development of chiral tridentate ligands has become increasingly important, enabling both reactivities and stereoselectivities in asymmetric hydrogenation. While noble metal catalysts with chiral tridentate ligands have made significant achievements, there is still a high demand for designing chiral tridentate ligands for earth abundant metal catalysts.
Article
Chemistry, Multidisciplinary
Tianjiao Hu, Lukas Lueckemeier, Constantin Daniliuc, Frank Glorius
Summary: The direct enantioselective hydrogenation of 2-quinolones using Ru(II)-NHC catalyst has been achieved, providing alkyl-, aryl- and halogen-substituted optically active dihydro-2-quinolones in high yields with moderate to excellent enantioselectivities. This reaction presents an efficient and atom-economic pathway to construct simple chiral 3,4-dihydro-2-quinolones.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Pablo Vazquez-Dominguez, Antonio Romero-Arenas, Rosario Fernandez, Jose Maria Lassaletta, Abel Ros
Summary: The catalytic hydroarylation of alkynes is a useful method for synthesizing functionalized alkenes with excellent control of regio- and stereochemistry. However, there is a scarcity of asymmetric methodologies in this field. In this study, an atroposelective Ir-catalyzed C-H hydroarylation of alkynes was developed, enabling the asymmetric synthesis of axially chiral heterobiaryl trisubstituted olefins with high yields and enantioselectivities up to 98% ee.
Article
Chemistry, Inorganic & Nuclear
Andreas Billion, Marcel Schorpp, Rebecca Feser, Manuel Schmitt, Lea Eisele, Harald Scherer, Takaaki Sonoda, Hajimu Kawa, Burkhard Butschke, Ingo Krossing
Summary: Weakly coordinating anions (WCAs) are used to stabilize and isolate reactive cations. The alkoxyaluminate-based WCA [Al(OC(CF3)(3))(4)](-) ([pf](-)) is widely used but can still be coordinated by small cations. A novel WCA [Al(OC10F15)(4)](-) ([pfAd](-)) is more stable due to its rigid core framework. Various salts containing [pfAd](-) were synthesized and characterized by spectroscopy and crystallography. The water stability of [pfAd](-) was demonstrated by the successful synthesis of Tl[pfAd] in a mixture of solvents.
DALTON TRANSACTIONS
(2023)
Article
Chemistry, Multidisciplinary
Yu Nie, Jing Li, Qianjia Yuan, Wanbin Zhang
Summary: In this work, we developed an iridium-catalyzed asymmetric hydrogenation of hydantoin and thiazolidinedione derived exocyclic alkenes using BiphPHOX as a ligand. The reaction showed excellent functional group tolerance and provided the hydrogenated products with high yields and enantioselectivities. Moreover, the hydrogenated product can be efficiently transformed into an intermediate for the synthesis of a HIV protease inhibitor.
CHINESE JOURNAL OF CHEMISTRY
(2022)
Article
Multidisciplinary Sciences
Bram B. C. Peters, Jia Zheng, Norman Birke, Thishana Singh, Pher G. Andersson
Summary: The authors developed a general iridium-catalyzed enantioconvergent hydrogenation method for a broad range of functionalized trisubstituted olefins. This method allows for efficient introduction of chirality into non-chiral substrates. The significance of this method lies in its ability to hydrogenate both isomerically pure alkenes and mixtures to yield the same major enantiomer in excellent enantiomeric excess, which is unusual in transition-metal catalyzed asymmetric hydrogenations.
NATURE COMMUNICATIONS
(2022)
Article
Biochemistry & Molecular Biology
Henrik Hill, Andris Elksnis, Per Lundkvist, Kumari Ubhayasekera, Jonas Bergquist, Bryndis Birnir, Per-Ola Carlsson, Daniel Espes
Summary: Gamma-aminobutyric acid (GABA) is an important inhibitory neurotransmitter found in the central nervous system and immune cells. Research has shown that GABA has immune-modulatory and beta-cell stimulatory effects and could potentially be used to treat type 1 diabetes. However, a study measuring the levels of GABA in T1D patients found that the levels were unchanged compared to healthy controls, suggesting that GABA secretion from beta-cells has minimal impact on systemic levels. The study also found correlations between GABA levels and certain cytokines and GAD-autoantibodies, indicating potential alterations in local GABA levels within pancreatic islets.
Article
Chemistry, Multidisciplinary
Bram B. C. Peters, Jia Zheng, Suppachai Krajangsri, Pher G. Andersson
Summary: This study reveals a novel reactivity of Crabtree-type complexes in the Ir-N,P-catalyzed hydrogenation of enones by adding benzamide and developing a reactive catalyst, resulting in a highly stereoselective reduction of enones.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Bram B. C. Peters, Pher G. Andersson, Somsak Ruchirawat, Winai Ieawsuwan
Summary: A highly efficient N,P-ligated iridium complex was developed for the synthesis of chiral tetrahydro-3-benzazepine motifs through catalytic asymmetric hydrogenation. The method exhibited excellent enantioselectivity and high yield, and was successfully applied in the synthesis of pharmaceuticals.
Article
Chemistry, Organic
Xingzhen Li, Bram B. C. Peters, Min Tan, Lei He, Jianping Yang, Pher G. Andersson, Taigang Zhou
Summary: In this study, an efficient and selective mono-N-alkylation method for sulfonamides was developed based on a borrowing hydrogenation strategy. The use of water as the only by-product makes this method more environmentally friendly, and it shows good tolerance towards various types of sulfonamides and alcohols.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Bram B. C. Peters, Pher G. Andersson
Summary: The translation discusses the application of chiral iridium complexes derived from Crabtree's catalyst in modern hydrogenation of olefins. Despite the pH neutrality of these precatalysts, the reaction mixtures become acidic under hydrogenation conditions. The paper explores the implications of this acidity on asymmetric hydrogenation and suggests opportunities for utilizing or eliminating the generated Bronsted acid.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Biochemistry & Molecular Biology
Wei Hu, Yaorui Hu, Yao Pei, Rongrong Li, Fuyi Xu, Xiaodong Chi, Jia Mi, Jonas Bergquist, Lu Lu, Luping Zhang, Chunhua Yang
Summary: A study found that there were 46 differentially expressed proteins between cervical carcinoma (CC) and normal tissues, with Integrin beta 6, PPP1CB, TMPO, PTGES3, and DTX3L significantly upregulated in CC, while Desmin was significantly downregulated. Silencing DTX3L could suppress CC cell proliferation, migration, invasion, and tumorigenesis, and enhance cell apoptosis. Furthermore, DTX3L silencing inhibited the activity of the PI3K/AKT/mTOR signaling pathway. These findings suggest that DTX3L may regulate CC progression through the PI3K/AKT/mTOR signaling pathway and could serve as a potential biomarker and therapeutic target for CC.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Chemistry, Multidisciplinary
Jianping Yang, Luca Massaro, Weigao Hu, Bram B. C. Peters, Norman Birke, Chayamon Chantana, Thishana Singh, Pher G. Andersson
Summary: Enantioconvergent catalysis allows for the conversion of different isomers of a starting material to a single highly enantioenriched product. The study presents a novel enantioselective double convergent 1,3-rearrangement/hydrogenation of allylic alcohols using an Ir-N,P catalyst, achieving high enantioselectivity and diastereomeric ratio. DFT calculations and control experiments demonstrate the significance of the 1,3-rearrangement in determining the stereochemistry of the reaction.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
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
Biochemistry & Molecular Biology
Sofia Persson, Kumari A. Ubhayasekera, Jonas Bergquist, Sahruh Turkmen, Inger Sundstroem Poromaa, Evangelia Elenis
Summary: Polycystic ovary syndrome (PCOS) is a common endocrine disorder among women, and hyperandrogenism can cause psychological morbidity and impaired quality of life. This study aimed to investigate whether hyperandrogenism persists into midlife and its impact on quality of life.
Article
Food Science & Technology
Julio Cesar Espana Amortegui, Heidi Pekar, Mark Dennis Chico Retrato, Malin Persson, Bengt Karlson, Jonas Bergquist, Aida Zuberovic-Muratovic
Summary: A LC-MS/MS method was developed for the simultaneous identification and quantification of cyanotoxins in edible bivalves. The method successfully detected and resolved two previously detected cyanotoxin congeners separately. The method showed limitations for certain cyanotoxins but overall was specific and robust for the parameters investigated. The method was applied to analyze mussel and oyster samples collected along the Swedish coast, and the results can contribute to future regulatory monitoring for cyanotoxins to ensure seafood safety.
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)
Article
Infectious Diseases
Anja Naas, Peng Li, Clas Ahlm, Elisabeth Aurelius, Josef D. Jarhult, Silvia Schliamser, Marie Studahl, Wenzhong Xiao, Jonas Bergquist, Gabriel Westman
Summary: This study investigated the temporal changes of the CSF proteome in patients with herpes simplex encephalitis (HSE) and its association with factors such as anti-NMDAR serostatus, corticosteroid treatment, brain MRI, and neurocognitive performance. The results showed that the composition and activation pathways of CSF proteins vary at different stages of the disease. Additionally, it was found that several proteins were less abundant in patients with anti-NMDAR seropositivity compared to seronegativity.
INFECTIOUS DISEASES
(2023)
Article
Chemistry, Analytical
Mark Dennis Chico Retrato, Siyuan Qiu, Anna Lundquist, Aida Zuberovic Muratovic, Farshid Mashayekhy Rad, S. J. Kumari A. Ubhayasekera, Jonas Bergquist
Summary: This study describes a simple and robust method for the identification and quantification of 22 fatty acids in TPN components using gas chromatography-mass spectrometry. The method was evaluated according to the guidelines from FDA, EMA, and ICH, and demonstrated good methodological performance. The developed method has potential applications for quality assurance and control of TPN products.
ANALYTICAL METHODS
(2023)
Article
Chemistry, Multidisciplinary
Jianping Yang, Sudipta Ponra, Xingzhen Li, Bram B. C. Peters, Luca Massaro, Taigang Zhou, Pher G. Andersson
Summary: In this study, a catalytic method for the asymmetric synthesis of enantioenriched products bearing fluoromethylated stereocenters with excellent yields and enantioselectivities was reported.
