Article
Chemistry, Organic
Huaibin Yu, Shuangshuang Wang, Jianjian Huang, Yu Fu, Manfred Wagner, Tanja Weil, Fangrui Zhong, Weining Zhao, Yuzhou Wu
Summary: This article reports the molecular design of a novel multifunctional reagent for light-controlled selective protein labeling. The molecule combines the functionalities of protein-ligand recognition, bioconjugation, ligand cleavage, and photoactivation. By releasing a highly electrophilic o-naphthoquinone methide, the reagent achieves proximity-driven selective labeling with the protein of interest while retaining its native function.
Article
Chemistry, Organic
Meng-Hao Yi, Hai-Shan Jin, Ru-Bing Wang, Li-Ming Zhao
Summary: An efficient copper-catalyzed cascade annulation of o-hydroxyphenyl propargylamines and pyrazolin-5-ones is described, leading to the rapid assembly of a series of valuable pyrano[2,3-c]pyrazoles with good yields across a wide range of substrates in a simple fashion. The mechanistic elucidation is well supported by control experiment and literature precedents.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Santosh J. Gharpure, Santosh K. Nanda, Dipak J. Fartade
Summary: This study demonstrates a facile synthesis of 1,4-heterocycle-fused quinoline motifs through intramolecular formal [4+2]-cycloaddition, involving tandem bond formation reactions and showing excellent functional group tolerance, leading to the synthesis of enantiomerically enriched compounds. Additionally, sulfoxide embedded quinolines were successfully transformed into pentacyclic 1,4-thiepino tethered indeno-quinoline scaffolds via Pummerer cyclization.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Marie-Ange Lespinasse, Kaiyao Wei, Justine Perrin, Matthias Winkler, Sieme Hamaidia, Alexis Leroy, Zuzana Macek Jilkova, Christian Philouze, Patrice N. Marche, Carlo Petosa, Jerome Govin, Anouk Emadali, Yung-Sing Wong
Summary: This study presents a simple, rapid, and cost-effective method to obtain new tetrahydroquinolines, which are useful in the pharmaceutical industry, particularly in the development of bioactive compounds for targeted therapy. This method provides access to tetrahydroquinolines with different configurations, and is enantioselective.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Review
Chemistry, Organic
Wang Haiqing, Yang Shuang, Zhang Yuchen, Shi Feng
Summary: The article discusses the application and related issues of o-QMs and summarizes the rapid development of catalytic asymmetric reactions using o-hydroxybenzyl alcohols as precursors. It also highlights the potential of these reactions in synthesizing chiral oxygen-containing heterocycles and arylmethane derivatives.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Barry M. Trost, Zhijun Zuo, Youliang Wang
Summary: The study presents a highly regio-, diastereo-, and enantioselective TMM cycloaddition reaction for the rapid assembly of 2-acyl-methylenecyclopentane in an atom-economic fashion. This intermolecular protocol provides easy and divergent access to a variety of structurally attractive cyclic adducts. The choice of a robust chiral diamidophosphite ligand, developed by the research group, was crucial for the success of this transformation.
Article
Chemistry, Organic
Shoya Nohara, Suguru Iwai, Naoya Yamaguchi, Yosuke Asada, Yusuke Kamiyama, Yuta Tanaka, Kenta Tanaka, Yujiro Hoshino
Summary: An organophotoredox-catalyzed oxidative synthesis of o-QMs for inverse-electron-demand [4+2] cycloaddition reactions has been developed. The reaction involves one-electron oxidation of 2-(sulfanyl-methyl)phenols by a thioxanthylium photoredox catalyst, generating o-QMs that react with various styrenes to produce chromanes with high regioselectivity.
Article
Biochemistry & Molecular Biology
Si-Jia Liu, Man-Su Tu, Kai-Yue Liu, Jia-Yi Chen, Shao-Fei Ni, Yu-Chen Zhang, Feng Shi
Summary: The catalytic asymmetric [2 + 4] cycloadditions of 3-vinylindoles with ortho-quinone methides using chiral phosphoric acid as the catalyst resulted in a series of indole-containing chroman derivatives with high structural diversity, overall high yields (up to 98%), good diastereoselectivities (up to 93:7 dr), and moderate to excellent enantioselectivities (up to 98% ee).
Article
Multidisciplinary Sciences
Lei Dai, Xueting Zhou, Jiami Guo, Xuan Dai, Qingqin Huang, Yixin Lu
Summary: The C-N axially chiral N-arylpyrrole motifs are important scaffolds in biologically active compounds, but their asymmetric synthesis is challenging. In this study, the authors developed a diastereo- and atroposelective synthesis of N-arylpyrroles enabled by light-induced phosphoric acid catalysis.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Henning J. Loui, Arun Suneja, Christoph Schneider
Summary: A synthetic method has been developed for the stereoselective (3 + 3)-cycloannulation of in situ generated carbonyl ylides with indolyl-2-methides, resulting in oxa-bridged azepino[1,2-a]indoles in one step. The products, with three stereogenic centers, were obtained with good stereoselectivity and yields, showcasing valuable heterocyclic complexity.
Article
Multidisciplinary Sciences
Waldemar Iwanek
Summary: This paper describes the reaction pathways and activation energies of alkoxybenzyl derivatives of resorcin[4]arene leading to the formation of o-quinomethide derivatives of resorcin[4]arene. The reaction mechanisms of o-QMR[4]A formation were proposed based on the calculated pathways. The energies of reactants, transition states, and products were calculated using different density-functional theory methods, and the theoretical reaction mechanisms were discussed in relation to experimental data.
ROYAL SOCIETY OPEN SCIENCE
(2022)
Article
Chemistry, Organic
Haiyu Sun, Yicheng He, Wusheng Guo
Summary: This study reports a Pd-catalyzed decarboxylative strategy for the asymmetric construction of spiro[4.5]deca-6,9-dien-8-ones. This approach utilizes modular vinyl methylene cyclic carbonates and p-quinone methides as reaction partners. The reaction can be performed at room temperature and generates CO2 as the sole by-product. The corresponding products feature otherwise synthetically challenging vicinal quaternary carbons, which create great potential for complexity and diversity. The stereochemistry of the reactions is controlled with diastereo- and enantioselectivity being up to >20 : 1 dr and 96 : 4 er.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Review
Chemistry, Multidisciplinary
Maria Tereza M. Martins, Flaviana Rodrigues F. Dias, Raphael Silva M. de Moraes, Marcos Felipe da Silva, Kaio R. Lucio, Karin D'Oliveira Goes, Patrick A. do Nascimento, Andre S. S. da Silva, Vitor F. Ferreira, Anna C. Cunha
Summary: This article provides an overview of multicomponent reactions (MCRs) that involve ortho-quinone methide intermediates (o-QM) and discusses their applications in organic synthesis and biological processes. QMs are generated through eliminative processes or photochemical reactions and can undergo various types of reactions.
Article
Chemistry, Multidisciplinary
Pei-Shan Wu, Yan-Cheng Liou, Gangababu Marri, Yi-Ru Chen, Jia-Rong Wu, Wenwei Lin
Summary: An efficient synthesis of chromeno[4,3-b]pyrrolidines has been developed via a mild base-catalyzed reaction, achieving excellent diastereoselectivity.
JOURNAL OF THE CHINESE CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Muhammad Sohail, Fujie Tanaka
Summary: We demonstrated that the loading amounts and concentrations of the reactant 1,3-cyclohexanedione have an impact on reaction rates and outcomes. Interestingly, in some cases, reactions with higher concentrations of 1,3-cyclohexanedione were slower than those with lower concentrations. By minimizing the use of cyclic 1,3-dione derivatives and adjusting the reaction concentration, we were able to reduce the acid catalyst to 0.1 mol% and obtain the desired products in high yields, while expanding the scope of the reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
