Review
Chemistry, Organic
Regina Westphal, Eclair Venturini Filho, Fabrizio Medici, Maurizio Benaglia, Sandro J. Greco
Summary: This review summarizes the latest developments in asymmetric domino reactions, with a focus on the preparation of spiro compounds. Discussions on the stereoselectivity of the transformations, reaction mechanisms, rationalization of the stereochemical outcome, and the applications of domino reactions to the synthesis of biologically active molecules and natural products are included.
SYNTHESIS-STUTTGART
(2022)
Review
Chemistry, Organic
Divyang M. Patel, Paras J. Patel, Hitendra M. Patel
Summary: This Review discusses pioneering advances in catalytic stereoselective multicomponent reactions for the preparation of spiro derivatives, highlighting the stereoselective reactions and catalytic mechanisms used in different reactions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Crystallography
Weiqing She, Zhenzhen Xu, Lianjie Zhai, Junlin Zhang, Jie Huang, Weiqiang Pang, Bozhou Wang
Summary: Due to the introduction of oxygen atoms, N-oxide energetic compounds possess unique advantages in terms of oxygen balance, detonation properties, and energy density, which have attracted extensive attention from researchers worldwide. This article provides a comprehensive review of the synthetic strategies for two categories of N-oxides, azine N-oxides and azole N-oxides, and discusses the reaction mechanisms of aromatic N-oxide frameworks and their applications in creating high-energy substances. Furthermore, the energetic properties of N-oxide energetic compounds are compared and summarized.
Article
Chemistry, Multidisciplinary
Christoph Etling, Giada Tedesco, Markus Kalesse
Summary: This study investigated the different reactivity of trienones under Lewis and Bronsted acids catalysis, resulting in novel Nazarov cyclization tandem reactions terminating oxyallyl cations by ene-type reactions. The bicyclic spiro compounds produced were shown to be useful intermediates for further functionalization. Furthermore, the tandem Nazarov/ene cyclization was found to be preferred over a Nazarov/[3+2] tandem reaction for all substrates, regardless of chain length.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Review
Chemistry, Multidisciplinary
Fengjuan Chen, Luo Liu, Wei Zeng
Summary: Compared with all-carbon parent compounds, incorporating Silicon into carboskeletons gives sila-analogues unique biological activity and physical-chemical properties. Silacycles have shown promising potential in biological chemistry, pharmaceuticals industry, and material chemistry. Therefore, the development of efficient methods to assemble versatile silacycles has been a topic of increasing concern. This review summarizes recent advances in the synthesis of silacycle-system, including transition metal-catalytic and photocatalytic strategies using various starting materials. The mechanistic aspects and features of these reaction methodologies are also highlighted.
FRONTIERS IN CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Poorna Chandrasekhar Settipalli, Shaik Anwar
Summary: A [2+2+2] annulation reaction between cyclohexanone, beta-nitrostyrene and 2-arylidene-1,3-indanedione has been successfully carried out to obtain multisubstituted spiro trans-decalinol derivatives at room temperature. This reaction process exhibits high chemical yields and excellent diastereoselectivity, resulting in the formation of multiple bonds and stereocenters through the Michael/nitro-Michael/Aldol process.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Applied
Tao Wang, Bo Huang, You-Qing Wang
Summary: Using chiral phosphoric acids as organocatalysts, a formal asymmetric (4+2) cycloaddition of 3-methylene isoindolinone and in situ-generated ortho-quinone methide substrates is achieved. This reaction allows the construction of spiro chroman-isoindolinones containing spiro-N,O-heterocycles with high enantioselectivity, with a broad substrate scope.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Review
Chemistry, Organic
Thomas C. Nugent, Alice E. Vos, Ishtiaq Hussain, Hussein Ali El Damrany Hussein, Falguni Goswami
Summary: This study provides an extensive introduction to amine-catalyzed aldol reactions with enantioselectivity for non-experts. It covers methodology limitations, mechanisms, physical-mechanical aspects, and considerations for ketone substrates. The study highlights 172 catalysts and provides experimental data for various ketone substrates. It also discusses the best reaction conditions and product formation for specific substrates. This research enables the selection of suitable reaction methods for given substrates and allows the targeted construction of substrates for selective product formation.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Yusaku Yoshiwara, Shunsuke Kotani, Makoto Nakajima
Summary: The asymmetric catalytic transformations of N-unprotected cyclic carboxyimides provide a direct route to access a variety of biologically valuable chiral compounds, such as succinimides, hydantoins, oxazolidinediones, and glitazones. The reaction involves the formation of a bis(trichlorosilyl) nucleophilic intermediate from cyclic carboxyimides, which then reacts with aldehydes through a cyclic transition state, leading to highly enantioselective aldol reactions. Additionally, N-unprotected carboxyimides can be chemoselectively activated, even in the presence of N-alkylated carboxyimides, for stereoselective and chemoselective aldol reactions via in situ silicon tetrachloride activation. The functionalized cyclic carboxyimides can be easily derivatized to various chiral building blocks without the need for unnecessary protection/deprotection steps.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Review
Chemistry, Applied
Cairong Wang, Ge Qiu, Chen Li, Kai Sun, Zhichuan Wang, Xin Wang
Summary: Carboxylic acid compounds are important structural units that exist widely in nature, and decarboxylative reactions have great significance in synthetic chemistry due to the non-flammable, non-toxic, and easy-to-remove byproduct carbon dioxide. Heterocyclic compounds are important backbones of various biologically active molecules, making research on new synthetic tactics for heterocyclic derivatives based on decarboxylative cyclization of great interest.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Venkati Bethi, Syeda Bakhtawar Zahra, Bapuaro D. Rupanawar, Fujie Tanaka
Summary: This article describes the regioselective aldol reactions of beta-methyl-substituted cyclic enone derivatives with isatins using a catalyst system composed of DBU, pyrrolidine, and DMSO. The reactions resulted in aldol products with bond formation at the methyl group of the beta-methyl-substituted cyclic enone derivatives. This method selectively affords gamma-position-reacted aldol products, expanding the scope of concisely synthesized 3-substituted 3-hydroxyoxindole derivatives.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Review
Chemistry, Organic
Durgesh Gurukkala Valapil, Manasa Kadagathur, Nagula Shankaraiah
Summary: The application of amino acids and small peptides as asymmetric organocatalysts in aldol and conjugate addition reactions has been a significant breakthrough in the past decade. Desired stereoselectivity in these reactions can be achieved through the tunable diversity elements present in amino acids/peptides. The literature is classified based on the use of single amino acids or peptides as catalysts, with detailed information on the design and recent applications of these catalysts.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Applied
Seoung-Mi Choi, Ju Hyun Kim
Summary: This review summarizes the progress made in the synthesis of 2H-pyrroles since 2000, including methods such as dearomatization of 1H-pyrrole, oxidation of pyrrolines or pyrrolidines, ring construction via catalytic cycloaddition, and rearrangement of 3H-pyrroles.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
V. Pratap Reddy Gajulapalli, Nandarapu Kumarswamyreddy, Kanduru Lokesh, Venkitasamy Kesavan
Summary: Utilizing a L-proline derived bifunctional thiourea organocatalyst, a highly functionalized 3,3'-disubstituted oxindole derivatives containing 3-acetyl coumarins and pyranocoumarin fused spirooxindoles can be synthesized with excellent yields (up to 95%) and enantioselectivities (up to 99% ee) in a broad substrate scope.
Article
Chemistry, Multidisciplinary
Ingolf Harden, Frank Neese, Giovanni Bistoni
Summary: The formation of Bronsted acid aggregates in asymmetric organocatalytic reactions has a significant impact on the stereo-controlling factors of the transformations. This study uses high-level quantum mechanical calculations to investigate the influence of catalyst structure and reaction conditions on the spontaneity of the aggregation process, shedding light on its importance.
Article
Chemistry, Analytical
Qian Kong, Peiwu Huang, Bizhu Chu, Mi Ke, Wendong Chen, Zhendong Zheng, Shanping Ji, Zongwei Cai, Pengfei Li, Ruijun Tian
ANALYTICAL CHEMISTRY
(2020)
Article
Chemistry, Analytical
Yiheng Mao, Peizhong Chen, Mi Ke, Xiong Chen, Shanping Ji, Wendong Chen, Ruijun Tian
Summary: The FISAP technology is a novel spintip-based AP-MS approach allowing for efficient sample processing and enhanced sensitivity, quantification performance, and reduced background interference. It is particularly useful for quantitative profiling of protein complexes when limited by starting material and affinity reagents, with potential applications in biomedical research and chemical biology.
ANALYTICAL CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Jian Yang, Dimitris Korovesis, Shanping Ji, Jan Pascal Kahler, Roeland Vanhoutte, Steven H. L. Verhelst
Summary: In this paper, a short and high-yielding route towards an FP-alkyne derivative is reported, which can be used for bioorthogonal 2-step detection of serine hydrolases. Additionally, red- and green-fluorescent FP-probes were constructed and applied in dual colour labelling of whole proteomes, showing potential for novel applications within ABPP.
ISRAEL JOURNAL OF CHEMISTRY
(2023)
Meeting Abstract
Biochemistry & Molecular Biology
Jonas De Backer, Shanping Ji, Xiaopeng Luo, Frank Van Breusegem, Steven Verhelst, Inge De Clercq
FREE RADICAL BIOLOGY AND MEDICINE
(2022)
Meeting Abstract
Biochemistry & Molecular Biology
Jonas De Backer, Shanping Ji, Xiaopeng Luo, Frank Van Breusegem, Steven Verhelst, Inge De Clercq
FREE RADICAL BIOLOGY AND MEDICINE
(2022)
Article
Biochemistry & Molecular Biology
Xiong Chen, Shanping Ji, Zheyi Liu, Xiao Yuan, Congsheng Xu, Ruxi Qi, An He, Heng Zhao, Haiping Song, Chunlei Xiao, Weina Gao, Peng R. Chen, Ray Luo, Pengfei Li, Fangjun Wang, Xueming Yang, Ruijun Tian
Summary: Identification of the tyrosine phosphorylation (pY)-dependent interactome of immune co-receptors is crucial for understanding signal pathways involved in immunotherapy. In this study, a photoaffinity-based chemical proteomic approach was used to dissect the motif-specific cytoplasmic interactomes of CD28, a critical immune co-receptor. The study identified specific interactions of phospholipase PLCG1 with the Y191 motif and the kinase PKCq with the previously undefined pY218 motif. This synthetic CD28(cyto)-based photoaffinity proteomic approach can be applied to study other immune co-receptors with multiple pY sites.
CELL CHEMICAL BIOLOGY
(2022)
Article
Chemistry, Medicinal
Feng Chen, Hong-Xia Ren, Yu Yang, Shan-Ping Ji, Zheng-Bing Zhang, Fang Tian, Lin Peng, Li-Xin Wang
