Article
Chemistry, Organic
Qi-Wen Shen, Wei Wen, Qi-Xiang Guo
Summary: The first catalytic asymmetric cascade Heck-alkylation reaction of NH2-unprotected amino acid esters with N-(2-iodophenyl)allenamides is reported in this work. The reaction proceeds smoothly using a combining catalytic system comprising a chiral aldehyde, a chiral palladium complex, and the Lewis acid ZnCl2, giving optically active alpha-alkyl tryptophan derivatives in moderate to good yields and excellent enantioselectivities. The target products can be converted into other structurally complex chiral indoles without the loss of enantioselectivities.
Article
Chemistry, Multidisciplinary
Ahreum Kim, Aram Kim, Sunjung Park, Sangji Kim, Hongil Jo, Kang Min Ok, Sang Kook Lee, Jayoung Song, Yongseok Kwon
Summary: A novel chiral phosphoric acid-catalyzed atroposelective Pictet-Spengler reaction of N-arylindoles has been reported, resulting in highly enantioenriched N-aryl-tetrahydro-beta-carbolines with axial chirality. The introduction of a hydrogen bond donor on the bottom aromatic ring, forming a secondary interaction with the phosphoryl oxygen, is crucial for achieving high enantioselectivity. The transformation is tolerant to a wide variety of substituents and can provide products with up to 98% ee.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Applied
Moreshwar B. B. Chaudhari, Prachi Gupta, Patricia Llanes, Miquel A. A. Pericas
Summary: The enantioselective Pictet-Spenlger reaction of tryptamines and diketo compounds catalyzed by a polymer-supported phosphoric acid (TRIP) has been achieved for the first time in continuous flow. A diverse library of quaternary tryptolines has been synthesized in 36-95% yield with 39-99% enantiomeric excess using this approach. The scalability of the reaction has been demonstrated in continuous flow, with a residence time of only 24 minutes. The robust immobilized catalyst has been recycled and reused multiple times in both batch and flow reactions. Synthesis of chiral precursors of Tadalafil, Iboga-type alkaloid (+)-Tabertinggine, and antimalarial spiroindolinones has been successfully achieved in both batch and continuous-flow reactions.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Xinpeng Cheng, Tianyou Li, Kaylaa Gutman, Liming Zhang
Summary: This study successfully synthesized alpha,beta-Butenolides with high enantiomeric excess using a novel Cu(I)-ligand cooperative catalysis, highlighting the importance of cooperation between the metal center and the ligand basic amino group. Moreover, it was found that other coinage metals such as Ag and Au can also play a similar role in this asymmetric isomerization chemistry.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Michele Retini, Francesca Bartoccini, Giovanni Zappia, Giovanni Piersanti
Summary: This article describes a new class of chiral thioureas that, in combination with 4-methoxybenzoic acid, promote enantioselective reactions. The formation of a chiral catalyst-anion complex was explored using H-1 NMR spectroscopy.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Jinlong Zhang, Zeng Gao, Jinlong Qian, Huameng Yang, Maosheng He, Gaoxi Jiang
Summary: A family of axially chiral azepine-containing seven-membered cyclic P,N-ligands, named Indole-azepinap, was prepared using L-alanine as an original chirality source. The direct chromatographic separation of two diastereomeric phosphine oxides on silica gel allowed easy accessibility of these ligands for further structural and electronic modifications. These Indole-azepinaps showed promising results in a Pd-catalyzed asymmetric allylic alkylation with high yields and moderate enantioselectivities.
Article
Chemistry, Multidisciplinary
Qing-Ru Zhao, Ru Jiang, Shu-Li You
Summary: An efficient strategy was developed to access a series of axially chiral styrenes by iridium-catalyzed allylic substitution and central-to-axial chirality transfer via olefin isomerization. The method provides a broad range of axially chiral styrenes with moderate to excellent yields and enantioselectivity, offering a powerful tool in asymmetric organic synthesis.
ACTA CHIMICA SINICA
(2021)
Article
Chemistry, Multidisciplinary
Jie Wang, Xiaotian Qi, Xiao-Long Min, Wenbin Yi, Peng Liu, Ying He
Summary: This study presents a novel approach for the synthesis of axially chiral styrenes through tandem iridium catalysis. The method allows for efficient and selective preparation of chiral ligands needed for asymmetric synthesis.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Thomas Varlet, Mateja Matisic, Elsa Van Elslande, Luc Neuville, Vincent Gandon, Geraldine Masson
Summary: A diastereodivergent and enantioselective synthesis of chiral spirocyclohexyl-indolenines with four contiguous stereo-genic centers was achieved through a chiral phosphoric acid-catalyzed cycloaddition. By carefully choosing reaction conditions, modular access to two different diastereoisomers with high enantioselectivities was obtained. The functional group manipulation of these compounds provides an efficient access to enantioenriched spirocyclohexyl-indolines and -oxindoles.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Wen-Kui Yuan, Bing-Feng Shi
Summary: An unprecedented enantioselective synthesis of spiro-gamma-lactams was achieved using a simple Co-II/chiral spiro phosphoric acid binary system, resulting in high levels of enantioselectivity. Additionally, a concise synthesis of an aldose reductase inhibitor was successfully carried out under this system.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Rayees Ahmad Naikoo, Rupesh Kumar, Parvesh Singh, Gaurav Bhargava
Summary: The manuscript discusses an efficient and atom economical synthesis method for pyrimido[4,5-b][1,4]benzodiazepin-4-ones through 7-endo-trig Pictet-Spengler type cyclisations. The synthetic approach involves the synthesis of different variants of 5-arylidene-amino-3H-pyrimidines and their cyclisations to afford biologically relevant functionalized benzodiazepine condensed pyrimidinones in good to excellent yields (82-94%).
SYNTHETIC COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Yu Hao, Zi-Hao Li, Zhi-Gang Ma, Ru-Xin Liu, Rui-Tian Ge, Quan-Zhe Li, Tong-Mei Ding, Shu-Yu Zhang
Summary: A novel axially chiral styrene-based organocatalyst with a pyrrole ring was designed and synthesized. This catalyst exhibited exceptional capabilities in producing densely substituted spirooxindoles with an alkyne-substituted quaternary stereogenic center via mild cascade Michael/cyclization reactions. The high conversion rates and exceptional enantioselectivity were attributed to the chiral matched pi-pi interactions and multiple H-bonds between the organocatalyst and substrates, as supported by experiments, X-ray structure analysis, and DFT calculations.
Article
Chemistry, Medicinal
Fernando Alonso, Agustin Galilea, Pau Arroyo Manez, Sofia L. Acebedo, Gabriela M. Cabrera, Marcelo Otero, Andrea A. Barquero, Javier A. Ramirez
Summary: Stereochemically complex polycyclic compounds were synthesized using a series of synthetic steps on steroid-derived scaffolds, combining fragments of natural products with novel scaffold structures, showing potential activity in treating tumors.
Article
Polymer Science
Janis V. Musso, Paul Gebel, Vincent Gramm, Wolfgang Frey, Michael R. Buchmeiser
Summary: A system for visible-light-controlled ring-opening metathesis polymerization (ROMP) was developed by combining thermally latent group 6 olefin metathesis initiators with a photoredox catalyst. This system can be applied to two-dimensional (2D) photolithography, and it exhibits high activity and stability without the need for thermal or UV post-curing.
Article
Chemistry, Organic
Wenxuan Zhang, Jiaying Sun, Zhendong Lian, Ran Song, Daoshan Yang, Jian Lv
Summary: Here, we report a chiral catalyst-catalyzed asymmetric reaction between 2-alkynyphenols and aromatic ethers. The reaction shows high yield and excellent enantioselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Qin Yin, Shou-Guo Wang, Xiao-Wei Liang, De-Wei Gao, Jun Zheng, Shu-Li You
Article
Chemistry, Applied
Xiao-Wei Liang, Chao Zheng, Shu-Li You
ADVANCED SYNTHESIS & CATALYSIS
(2016)
Article
Chemistry, Multidisciplinary
Chuan Liu, Ji-Cheng Yi, Xiao-Wei Liang, Ren-Qi Xu, Li-Xin Dai, Shu-Li You
CHEMISTRY-A EUROPEAN JOURNAL
(2016)
Review
Chemistry, Multidisciplinary
Xiao-Wei Liang, Chao Zheng, Shu-Li You
CHEMISTRY-A EUROPEAN JOURNAL
(2016)
Article
Chemistry, Multidisciplinary
Xiao-Wei Liang, Xiaoling Chen, Zhiguo Zhang, Shu-Li You
CHINESE CHEMICAL LETTERS
(2018)
Article
Chemistry, Multidisciplinary
Xiao-Wei Liang, Yue Cai, Shu-Li You
CHINESE JOURNAL OF CHEMISTRY
(2018)
Article
Chemistry, Organic
Quan Cai, Chuan Liu, Xiao-Wei Liang, Shu-Li You
Article
Chemistry, Organic
Quan Cai, Xiao-Wei Liang, Shou-Guo Wang, Jun-Wei Zhang, Xiao Zhang, Shu-Li You
Article
Chemistry, Multidisciplinary
Zi-Lei Xia, Chao Zheng, Xiao-Wei Liang, Yue Cai, Shu-Li You
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Article
Chemistry, Multidisciplinary
Xiao-Wei Liang, Yunlong Zhao, Xu-Ge Si, Meng-Meng Xu, Jia-Hao Tan, Zhi-Mao Zhang, Cheng-Gong Zheng, Chao Zheng, Quan Cai
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2019)
Review
Chemistry, Multidisciplinary
Yuxin Zhou, Xiao-Wei Liang
Summary: This review gives a brief overview of recent applications of the solid-phase strategy in the total synthesis of antibiotics, which have become crucial in overcoming bacterial resistance and simplifying isolation and purification procedures.
Review
Chemistry, Organic
Zhipeng Zhang, Ying-jun Zhou, Xiao-Wei Liang
ORGANIC & BIOMOLECULAR CHEMISTRY
(2020)
Article
Chemistry, Multidisciplinary
Xiao-Wei Liang, Chuan Liu, Wei Zhang, Shu-Li You
CHEMICAL COMMUNICATIONS
(2017)
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
