Article
Chemistry, Organic
Shuheng Xu, Linwei Zeng, Sunliang Cui
Summary: The Diels-Alder (DA) reaction and hetero-Diels-Alder (HDA) reaction are powerful methods for constructing carbocycles and heterocycles. This study presents an integrated building block that combines both DA and HDA reactions, utilizing triazenyl dienes to undergo the DA reaction and the newly released alkene moiety and triazene to engage in the HDA reaction.
Article
Chemistry, Multidisciplinary
Shuang Qiu, Xin Zhang, Chaopeng Hu, Hongxu Chu, Qianli Li, David A. Ruiz, Liu Leo Liu, Chen-Ho Tung, Lingbing Kong
Summary: In this study, we reveal the reactivity of aryliminoboranes via BNCC π conjugation, enabling the dearomative Diels-Alder-like reactions with aldehydes. This reaction features mild conditions, catalyst-free, and exhibits a broad substrate scope and good functional group tolerance.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Wynter E. G. Osminski, Zhenjie Lu, Wenjun Zhao, Aliakbar Mohammadlou, Xiaopeng Yin, Emily C. Matthews, Virginia M. Canestraight, Richard J. Staples, Connor J. Allen, Jennifer S. Hirschi, William D. Wulff
Summary: Boroxinate complexes of VAPOL and VANOL serve as a versatile staging arena for asymmetric catalysis, where multiple chiral catalysts can be rapidly assembled from various alcohols and bis-phenol ligands for screening of catalyst activity. The effect of variations in the steric and electronic properties of the phenol/alcohol component of the boroxinate catalyst on asymmetric induction in catalytic reactions is explored in this study. The mechanism of the boroxinate catalyst in catalytic asymmetric aziridination reaction involves hydrogen bonding to the boroxinate core rather than functioning as a Lewis acid.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Takahiro Suzuki, Soichiro Watanabe, Wataru Ikeda, Susumu Kobayashi, Keiji Tanino
Summary: Chloropupukeananin family of compounds are complex bioactive natural products with unique skeletons. The biosynthesis involves a Diels-Alder reaction triggered by specific compounds, although the enzymes responsible have not been identified. A biomimetic synthesis of chloropupukeananin and chloropupukeanolide D has been successfully achieved, indicating a potential role of Diels-Alderases in the biosynthesis of this compound family.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Victor Laina-Martin, Jose A. Fernandez-Salas, Jose Aleman
Summary: Cycloaddition reactions, particularly Diels-Alder reactions, are regarded as powerful methodologies for building carbon-carbon bonds. The inverse-electron-demand hetero-Diels-Alder reactions have been a significant breakthrough for synthesizing heterocyclic compounds. Among them, the organocatalytic enantioselective version has been extensively studied due to its asymmetric construction of diversely functionalized scaffolds under green chemistry conditions.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Fabian Hofmann, Cornelius Gaertner, Martin Kretzschmar, Christoph Schneider
Summary: Aza-Diels-Alder reactions are direct processes for constructing N-heterocycles, with inherent atom economy and stereospecificity. Intramolecular strategies can form bicyclic core structures with up to three stereocenters in a single step. The combination of this concept with chiral Bronsted acid bound ortho-quinone methide imines generates a range of interesting fused tetrahydroquinolines in a diastereo- and enantioselective manner.
SYNTHESIS-STUTTGART
(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
Ju-Hyung Chae, Minyeong Choi, Semin Son, Su-Min Ko, In-Hwan Lee
Summary: Precise control of multiple structural parameters associated with vinyl polymers is important for producing materials with the desired properties and functions. The development of living polymerization methods has provided a way to control the various structural parameters of vinyl polymers, but controlling their sequence and regioregularity remains challenging. In this study, we report a scalable and modular synthesis of cyclic monomers through a one-step protocol using readily available vinyl precursors. The living cationic ring-opening polymerization of these cyclic monomers allows for the synthesis of vinyl polymers while controlling multiple factors, such as molecular weight, dispersity, alternating sequence, regioregularity, and end-group functionality. The synthesized vinyl polymers exhibit unique thermal properties and undergo fast photodegradation even under sunlight.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Bartosz Jedrzejewski, Mateusz Musiejuk, Justyna Doroszuk, Dariusz Witt
Summary: The study has developed simple and efficient methods for the synthesis of unsymmetrical vinyl disulfides with additional functional groups under mild conditions. These methods involve reactions between S-vinyl phosphorodithioate and thiotosylates, allowing for the synthesis of vinyl disulfides with various additional functionalities. Furthermore, the vinyl disulfides react with transient o-iminothioquinones in an inverse electron-demand [4+2] cycloaddition to yield benzo[b][1,4]thiazine derivatives.
Article
Chemistry, Organic
Ramazan Kocak, Arif Dastan
Summary: Novel polycyclic pi-conjugated dihydropyridazines, pyridazines, and pyrroles were synthesized using various reactions, with all dihydropyridazines showing absorbance and emission at long wavelengths.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Juan Francisco Rodriguez-Caro, Maria M. Afonso, Jose Antonio Palenzuela
Summary: A short, simple, and general synthesis of 5,8-disubstituted indolizidines, the largest family of indolizidines isolated from amphibian skin, is presented in this paper. These compounds exhibit interesting biological activities such as noncompetitive blockers of nicotinic receptors. The selectivity of the synthesis process is explained based on computational studies. The concise synthesis of indolizidine alkaloid 181B from a hetero Diels-Alder reaction was accomplished in four steps.
Article
Chemistry, Multidisciplinary
Yubiao Hong, Tianjiao Cui, Sergei Ivlev, Xiulan Xie, Eric Meggers
Summary: This study introduces a new chiral-at-iron catalyst that can achieve high enantioselectivities in asymmetric reactions by increasing steric hindrance at the catalytic site. The catalyst was applied to the inverse electron demand hetero-Diels-Alder reaction and showed excellent diastereoselectivities and enantioselectivities. Other electron rich dienophiles, such as vinyl azide, are also suitable for this catalyst.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
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, Multidisciplinary
Laura Cunningham, Patrick J. Guiry
Summary: This article describes the synthesis of planar chiral diols through a simple route, which are catalytically active and produce highly selective products in asymmetric reactions. The likely transition state is confirmed by X-ray crystallographic analysis, and both enantiomers of the product can be obtained by varying the substitution of the catalyst.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Multidisciplinary Sciences
Xiangfeng Lin, Xianghui Liu, Kai Wang, Qian Li, Yan Liu, Can Li
Summary: The study introduces a novel catalytic system for an asymmetric hetero-Diels-Alder reaction, leading to the synthesis of diverse tetracyclic isochroman frameworks with excellent stereoinduction. The key reaction involves a stepwise pathway, with steric hindrance playing a role in enantioselectivity.
NATURE COMMUNICATIONS
(2021)
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)