Article
Chemistry, Multidisciplinary
Chao Wu, Baode Ma, Gen-Qiang Chen, Xumu Zhang
Summary: In this study, an efficient synthetic method for chiral beta-heteroaryl amino alcohols was developed. The reaction showed high enantioselectivity and yield, and was successfully used for the gram-scale synthesis of important intermediates.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Hai-xuan Liu, Fei Ji, Yu Chen, Ya Gao, Jun-ke Wang, Ming-zhi Zhang, Fang Liu, Qiang Sha
Summary: This study reports a divergent synthesis of a variety of 2 alpha- and 5 alpha-substituted furan derivatives from 2-hydroxy-1,4-diones, achieved through selective reactions using different substrates and catalysts. The products showed moderate antifungal activity against Rhizoctorzia solani and Botrytis cinerea.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Applied
Jiali Fang, Yiping Xu, Hanwen Ren, Chenming Huang, Wenhe Zhang, Xian Jia, Song You, Bin Qin
Summary: In this study, we developed a three-step chemoenzymatic cascade route for the synthesis of chiral miconazole analogues. By optimizing reaction conditions, the method eliminated the need for isolation of intermediates and avoided the use of metal catalysts, achieving high yields and impressive stereoselectivities.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Yan He, Qimeng Liu, Tian Gong, Yunfei Liu, Xinying Zhang, Xuesen Fan
Summary: A convenient synthesis protocol for alpha-substituted-beta-oxo azaheterocycles has been developed using oxoammonium salt-promoted cascade reaction. Nucleophiles such as acetyl or cyano group-containing active methylene compounds or morpholines were reacted with saturated cyclic amines, leading to the formation of different intermediates. The chemoselectivity of these reactions was investigated through experimental studies and DFT calculations.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Jinzheng Wang, Du'an Lin, Ming Liu, Han Liu, Pilar Blasco, Zhenquan Sun, Yan Chu Cheung, Sheng Chen, Xuechen Li
Summary: By streamlining solution phase-solid phase synthesis and chemical ligation-mediated peptide cyclization, the total synthesis of mannopeptimycin beta was achieved. Mannoeloptimycin beta, a cyclic glycopeptide, exhibits antibacterial activity against antibiotic-resistant Gram-positive pathogens.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Hang Han, Bingbin Zhu, Xiaofan Du, Yu Zhu, Chuanming Yu, Xinpeng Jiang
Summary: A novel reaction for the synthesis of 1-azido-3-heteroaryl bicyclo[1.1.1]pentanes via azidoheteroarylation of [1.1.1]propellane is reported. This strategy allows for the direct installation of an azido group, providing an efficient route for synthetic organic chemistry applications.
Article
Chemistry, Organic
Man Yang, Xiaotong Chang, Shengqing Ye, Qiuping Ding, Jie Wu
Summary: A catalyst-, base-, and additive-free three-component reaction was developed for the synthesis of heteroaryl-substituted sulfonyl compounds under mild conditions. Various functional groups were well tolerated in this transformation, demonstrating a broad substrate scope. The preliminary mechanistic investigation indicated that the reaction proceeds through a radical process.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Julien Escudero, Pieter Mampuys, Carl Mensch, Charles B. Bheeter, Robby Vroemans, Romano V. A. Orru, Jeremy Harvey, Bert U. W. Maes
Summary: o-Phenylene N-substituted iminocarbonates can be obtained through aerobic Ni-catalyzed reaction of readily available catechols and isocyanides. The choice of oxidant and absence of base are crucial to avoid unwanted catechol oxidation. This method is generally applicable to other oxidation-sensitive aromatic 1,2-bisnucleophiles, providing a new approach to important bicyclic heterocycles.
Article
Chemistry, Applied
Andres Vazquez-Lopez, James E. Allen, Sarah E. Wengryniuk
Summary: A metal-free olefin diamination via a heterocyclic group transfer (HGT) reaction of I(III) N-HVI reagents has been reported, resulting in the synthesis of 3-aminopiperidines with high selectivity. The HGT strategy utilizes heteroarenes as oxidatively masked amine nucleophiles to produce (hetero)arylonium salt products, which can be easily isolated and further diversified. Mechanistic studies suggest that the 6-endo selectivity is attributed to the ring opening of an intermediate aziridinium ion.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Bowen Li, Bangke Luo, He Yang, Wenjun Tang
Summary: This study reports an efficient palladium-catalyzed Heck reaction for the synthesis of heterocycles with α-heteroaryl substitution. The method exhibits a broad substrate scope and excellent functional group compatibility. The use of a sterically bulky ligand containing an anthryl moiety is crucial for this transformation. Additionally, an asymmetric variant of the Heck reaction has been achieved, enabling the efficient asymmetric synthesis of (S)-nicotine and its analogues via a cationic palladium pathway.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Yufei Song, Zhaolin Quan, Zhengkai Chen, Xiao-Feng Wu
Summary: A facile and straightforward method for the synthesis of fused quinoxalinones has been achieved via palladium-catalyzed cascade carbonylative cyclization. The transformation involves cascade carbonylation, acyl azide formation, Curtius rearrangement, and intramolecular cyclization. The obtained heterocycle products can be easily converted into structurally diverse valuable compounds, demonstrating the synthetic utility of the developed protocol.
Article
Chemistry, Organic
Ashish Kumar Sahoo, Anjali Dahiya, Bubul Das, Ahalya Behera, Bhisma K. Patel
Summary: This study presents a novel green-light-induced regioselective difunctionalization of terminal alkynes using sodium arylsulfinates, carboxylic acids or NH4SCN, and eosin Y as the photocatalyst. The mechanism involves a radical-induced iodosulfonylation followed by a base-mediated nucleophilic substitution. The methodology allows for the synthesis of highly functionalized (Z)-beta-substituted vinylsulfones with tolerance to structurally diverse substrates, providing a practical pathway for C-O and C-S bond assembly.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Philip R. D. Murray, Isabelle Nathalie-Marie Leibler, Sandrine M. Hell, Eris Villalona, Abigail G. Doyle, Robert R. Knowles
Summary: We introduce a two-component annulation strategy that involves the combination of aryl alkenes and redox-active radical precursors bearing tethered nucleophiles, enabling the synthesis of a diverse collection of five- and six-membered saturated heterocycles. This strategy employs an Ir(III) photocatalyst and a Bronsted acid under visible-light irradiation. The synthesis involves reductive proton-coupled electron transfer, radical addition to alkene, oxidative radical-polar crossover, and cyclization of the tethered nucleophile. This approach allows the easy access to a wide range of heterocycles, including pyrrolidines, piperidines, tetrahydrofurans, morpholines, delta-valerolactones, and dioxanones. It is amenable to gram-scale preparation and complex fragment coupling.
Article
Chemistry, Inorganic & Nuclear
Clement R. P. Millet, Jurgen Pahl, Emily Noone, Kang Yuan, Gary S. Nichol, Marina Uzelac, Michael J. Ingleson
Summary: Dimeric aminoboranes can be activated by different reagents to form isolable compounds with B2N2 cores. The reactivity of these compounds in alkyne hydroboration depends on their structure. The B2N2-based bis-boranes are more reactive than the mono-boron systems.
Article
Chemistry, Organic
Min Tao, Jiasheng Qian, Zuanguang Chen, Lin-Kun An, David M. Wilson, Jianbo Liu
Summary: We report the one-pot synthesis of N-CF3 heteroaryl amides from heteroaryl carboxylic acids and sterically hindered isothiocyanates, including various amino acid analogues, in the presence of AgF. This method represents a complementary approach to our previous work and allows modification of previously inaccessible structures, including alpha-tertiary amines and N-CF3-modified pharmaceuticals.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
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)
