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
Multidisciplinary Sciences
Min Jin, Congyun Tang, Yingying Li, Shuai Yang, Ying-Tao Yang, Lin Peng, Xiao-Nian Li, Wenjing Zhang, Zhili Zuo, Fabien Gagosz, Liang-Liang Wang
Summary: In this study, the authors present a catalytic asymmetric inverse-electron-demand-hetero-Diels-Alder reaction between neutral alkenes and alpha, beta-unsaturated ketones or aldehydes using a chiral phosphoric acid catalyst. This complex transformation allows for the formation of chiral fused heterocycles containing a central tetrahydropyran ring with high regio-, diastereo- and enantioselectivity. The stereocontrol achieved in this process is attributed to a key remote double hydrogen atom bonding interaction between the linear substrate and the catalyst.
NATURE COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Zhipeng Guan, Xingxing Zhong, Yayu Ye, Xiangwei Li, Hengjiang Cong, Hong Yi, Heng Zhang, Zhiliang Huang, Aiwen Lei
Summary: A new photocatalytic approach for the synthesis of chroman compounds is reported in this study. This method offers mild reaction conditions and high selectivity, making it a potential application in the field of medicinal chemistry.
Article
Chemistry, Multidisciplinary
Shuxuan Liu, Ka Lok Chan, Zhenyang Lin, Jianwei Sun
Summary: This article reports the use of extended quinone methides with carbonyl and methide units distributed across two different rings as intermediates for asymmetric synthesis. By using suitable chiral phosphoric acids, the first asymmetric process involving such intermediates was achieved. These processes provide a rapid and highly enantioselective access to previously less accessible remotely chiral naphthols and naphthylamines. Control experiments and DFT calculations reveal important insights into the reaction mechanism, which likely involves the role of two phosphoric acid molecules in the enantiodetermining transition states. This work serves as a proof of concept for the exploitation of new types of extended quinone methides as versatile intermediates for asymmetric synthesis, offering a new platform for the efficient construction of remote benzylic stereogenic centers of aromatic compounds.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Multidisciplinary
Masao Ohashi, Dan Tan, Jiayan Lu, Cooper S. Jamieson, Daiki Kanayama, Jiahai Zhou, K. N. Houk, Yi Tang
Summary: The synthesis of cis-decalin structures using [4 + 2] cycloaddition with high stereoselectivity is challenging. In this study, we investigated the biosynthetic pathway of the fungal natural product fischerin (1) and identified a novel pericyclase, FinI, which catalyzes this reaction. The cocrystal structure of FinI, a predicted O-methyltransferase, with the product and SAM provides valuable insights into the natural formation of cis-decalin.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2023)
Article
Chemistry, Organic
Ganesh Shivayogappa Sorabad, Ding-Yah Yang
Summary: A facile and regioselective Lewis acid-catalyzed cascade annulation of o-hydroxyphenyl propargyl amines with 4-hydroxycoumarin to afford furano[3,2-c]coumarin and pyrano[3,2-c]coumarin derivatives is reported. The reaction proceeds through the conjugate addition of 4-hydroxycoumarin to the in situ-generated alkynyl o-quinone methide followed by intramolecular 5-exo-dig and 6-endo-dig annulation to form furano[3,2-c]coumarins and pyrano[3,2-c]coumarins, respectively. The prepared o-hydroxyl substituted pyrano[3,2-c]coumarins can be easily transformed into the corresponding coumarin-derived dioxabicycles by acid-mediated cyclization.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Kai Li, Shengli Huang, Tianyu Liu, Shiqi Jia, Hailong Yan
Summary: We demonstrated an organocatalytic asymmetric dearomatizing hetero-Diels-Alder reaction of benzene derivatives, which allows the synthesis of diverse stereochemically complex compounds and oxahelicenes. The high complexity and three-dimensionality of the products are crucial for their potential applications in materials science and drug discovery.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Organic
Julia O. Strelnikova, Alexander N. Koronatov, Nikolai Rostovskii, Alexander F. Khlebnikov, Olesya Khoroshilova, Mariya A. Kryukova, Mikhail S. Novikov
Summary: The domino reaction catalyzed by Rh-2(Piv)(4) leads to the formation of N-sulfonylated (Z)-2-(2-aminovinyl)imidazoles, providing a direct and flexible access to the desired compounds.
Article
Chemistry, Multidisciplinary
Jianyang Dong, Andreas Ostertag, Christof Sparr
Summary: In this study, the accessibility of atropisomeric o-quinodimethanes and the enantioselective synthesis of their precursors were described. The catalyst-stereocontrolled [2+2+2] cycloaddition and subsequent stereospecific Diels-Alder reactions enabled the synthesis of enantioselective compounds with high selectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Yan Jiang, Hao-Jie Ma, Xue-Long Wang, Yi Yang
Summary: A Yb(OTf)(3)-catalyzed formal (4 + 3) cycloaddition reaction was successfully achieved using donor-acceptor cyclopropanes and 3-benzylideneindoline-2-thiones as reactants. Functionalized 5,10-dihydro-2H-thiepino[2,3-b]indole derivatives were synthesized with good yields and moderate to good diastereoselectivity. This reaction represents the first (4 + 3) cycloaddition of 3-benzylideneindoline-2-thiones.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Alemayehu Gashaw Woldegiorgis, Haorui Gu, Xufeng Lin
Summary: The organocatalytic asymmetric reactions of C2-unsubstituted racemic naphthyl-indoles with orthoalkynylnaphthols were used to synthesize axially chiral styrenes connected to an axially chiral naphthyl-indole unit. By employing chiral phosphoric acid as the catalyst, these axially chiral styrenes were obtained in good yields (up to 96%) and excellent stereoselectivity (up to >99.9% ee, >20:1 dr, and >99:1 E/Z) under mild conditions. Furthermore, further synthetic transformations were achieved with high yields and excellent stereocontrol.
Article
Nanoscience & Nanotechnology
Zhipeng Ouyang, Diana Tranca, Yazhen Zhao, Zhenying Chen, Xiaobin Fu, Jinhui Zhu, Guangqun Zhai, Changchun Ke, Emmanuel Kymakis, Xiaodong Zhuang
Summary: A novel CMP enriched with C=O units was synthesized through a highly efficient Diels-Alder reaction, exhibiting a fused carbon backbone and a semiconductive characteristic. When used as organic electrode material in LIBs, these CMPs showed remarkable cycling stability, superior lithium-ion diffusion coefficient, and excellent rate capability.
ACS APPLIED MATERIALS & INTERFACES
(2021)
Article
Chemistry, Physical
Jinbo Zhang, Manli Ma, Rong Zhou, Hongqiang Chu, Xue Wang, Shaojie Wang, Huhu Tian, Zhipeng Yan, Mingtao Li, Zhongyan Wu, Bin Li, Jiafeng Yan, Lan Anh Thi Nguyen, Rongxing Cao, Guoqing Wu, Xianghua Zeng, Hao-Li Zhang, Jaeyong Kim, Lin Wang, Yongjun Tian
Summary: In this study, it is demonstrated using multiple characterization techniques that the bowl-shaped clusters C18Te3Br4(Bu-O)(6) may undergo a Dehydro-Diels-Alder (DDA) reaction at high pressure, resulting in crystalline carbon materials with different transport properties.
Article
Chemistry, Organic
Nan-Fang Mo, Ying Zhang, Zheng-Hui Guan
Summary: An asymmetric organocatalyzed three-component Povarov reaction has been developed to construct azaspirocycles. A chiral phosphoric acid catalyst with a unique structure was highly efficient in the reaction, leading to a wide range of azaspirocycles in high yields and excellent enantioselectivities. This reaction has expanded the scope of the traditional Povarov reaction.
Article
Chemistry, Organic
Gary L. Points, Christopher M. Beaudry
Summary: Substituted carbazoles are efficiently synthesized from 3-triflato-2-pyrones and alkynyl anilines, allowing for multiple substituents with complete control of regiochemistry, resulting in complex substitution patterns. This strategy can also be applied to prepare substituted bicarbazoles and related biaryls, and has been demonstrated in the synthesis of the carbazole natural product clausine C.
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
