Article
Chemistry, Multidisciplinary
Yulin Han, Anni Qin, Qian Zhang, Xue Zhang, Hui Qian, Shengming Ma
Summary: The Rh-catalyzed reaction allows for the efficient synthesis of cis-fused bicyclic products with excellent selectivity and tolerance towards synthetically useful functional groups. The proposed mechanism involves the rapid racemization of the allene moiety in the starting materials.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Hiroto Uno, Koki Kawai, Taichi Araki, Motoo Shiro, Norio Shibata
Summary: Gem-difluoromethylene moieties are attractive in medicinal chemistry due to their ability to mimic other more ubiquitous functional groups. A novel asymmetric method for their construction was developed, allowing easy access to chiral 1,3-dioxanes that contain a tetrasubstituted difluoroalkyl stereogenic center. The gem-difluoro substitution pattern promotes the reaction, and various substrates were suitable for this method.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Jian-Hua Liu, Qing Zhou, Yao Lin, Zhu-Lian Wu, Tian Cai, Wei Wen, Yan-Min Huang, Qi-Xiang Guo
Summary: In this study, a highly efficient atom-economic asymmetric alpha-allylation method using chiral-aldehyde/palladium catalyst was reported. This method enables the asymmetric alpha-allylation of different 1,3-dienes and allenes with N-unprotected amino acid esters, leading to the synthesis of alpha,alpha-disubstituted chiral alpha-amino acid esters with high efficiency, good yields, and stereoselectivities. No N-allylation byproducts were observed in these reactions. Two reaction models were proposed based on mechanistic control experiments. Overall, this work demonstrates a new approach for preparing structurally diverse chiral amino acids and provides insights for developing chiral-aldehyde catalytic systems.
Article
Chemistry, Physical
Can Gao, Xunhua Wang, Jitian Liu, Xiaoxun Li
Summary: This study presents a palladium-catalyzed asymmetric [4 + 4] cycloaddition, allowing for efficient synthesis of highly stereochemically controlled nitrogen-heterocyclic compounds. The method provides good regio-, stereo-, and enantioselectivity, with the ability to tolerate complex substrates derived from natural products.
Article
Chemistry, Multidisciplinary
Xian-Xiao Chen, Hao Luo, Ye-Wei Chen, Yang Liu, Zhi-Tao He
Summary: Chain walking has been an efficient method for the functionalization of inert C(sp(3))-H bonds, but it has limitations on mono-olefin migration and functionalization. In this study, we demonstrate the feasibility of tandem directed simultaneous migrations of remote olefins and stereoselective allylation. The use of palladium hydride catalysis and secondary amine morpholine as a solvent is crucial for achieving high substrate compatibility and stereochemical control.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Physical
Kai Wang, Xiangfeng Lin, Yan Liu, Can Li
Summary: This study presents a novel catalytic asymmetric [4+2] cycloaddition reaction, achieved through direct allylic C-H functionalization with high diastereoselectivities and enantioselectivities to synthesize hydroquinolines.
Article
Chemistry, Organic
Yang-Zi Liu, Zhongao Wang, Zesheng Huang, Wu-Lin Yang, Wei-Ping Deng
Summary: The study demonstrates that sulfonyl-TMM can serve as an effective surrogate of naked TMM, showing high reactivity, exclusive regioselectivity, and excellent stereoselectivity.
Article
Chemistry, Multidisciplinary
Yu-Qing Xiao, Miao-Miao Li, Zheng-Xin Zhou, Yu-Jie Li, Meng-Yue Cao, Xiao-Peng Liu, Hai-Hua Lu, Li Rao, Liang-Qiu Lu, Andre M. Beauchemin, Wen-Jing Xiao
Summary: This article describes a palladium-catalyzed highly diastereo- and enantioselective (3+2) cycloaddition reaction, which successfully synthesizes a variety of chiral five-membered heterocycles. The key to the success of this reaction is the remote stereoinduction through hydrogen bond, addressing the challenge of generating chiral quaternary stereocenters using substrates with two different acceptors.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Yating Dai, Hongchun Huang, Shuangshuang Liang, Yanli Yin, Xu Ban, Xiaowei Zhao, Zhiyong Jiang
Summary: In this study, an enantioselective intermolecular [3 + 2] cycloaddition of N-arylcyclopropylamines with 2-aryl acrylates/ketones and cyclic ketone-derived terminal olefins via asymmetric photoredox catalysis was reported. A dual catalyst system involving DPZ and a chiral phosphoric acid was effective for the transformations, leading to a wide array of valuable cyclopentylamines with high yields, ee's, and drs. Elaborate modulation of the ester group of 2-aryl acrylates was shown to be effective in improving reactivity, thereby enabling the success of the transformations.
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)
Article
Chemistry, Applied
Chang Yoon Lee, Yong Il Kwon, Hyun Sun Jang, Sumin Lee, Yoo Lim Chun, Junyang Jung, Sung-Gon Kim
Summary: The first organocatalytic asymmetric [4+3]-cycloaddition of 2-aminophenyl alpha,beta-unsaturated carbonyls with in situ generated azaoxyallyl cations was successfully developed, leading to the synthesis of enantioenriched functionalized seven-membered 1,4-benzodiazepine-3-ones. This method was also extended to the first asymmetric [4+3]-cycloaddition of delta-hydroxy alpha,beta-unsaturated carbonyls, providing 1,4-oxazepanes in one step under mild conditions. Some of the novel adducts showed promising bioactivity in preventing peripheral nerve degeneration.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Sundaravel Vivek Kumar, Patrick J. Guiry
Summary: We have developed a facile synthetic route for a novel series of imidazolinyl-[2.2]paracyclophanol (UCD-Imphanol) ligands with central and planar chirality. These ligands showed excellent activities and selectivities in asymmetric reactions, leading to enantioenriched pyrrolidines with high yields.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Barry M. Trost, Zhijun Zuo
Summary: A novel Pd-0-catalyzed highly selective [3+2] spiroannulation reaction has been developed for rapid assembly of a new class of [5,5] spirocyclic carbo- and heterocycles. The regioselectivity of the reaction can be controlled by fine-tuning the Pd-pi-allyl intermediate, with excellent toleration of various coupling partners and enantioselectivities demonstrated through further transformations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Organic
Wang Yuchao, Liu Jinbiao, He Zhitao
Summary: This paper summarizes the development, advancements and mechanistic features of palladium-catalyzed asymmetric hydrofunctionalizations of conjugated dienes. Based on the types of allylic stereogenic centers constructed, the review is divided into six parts.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Fei Tian, Wu-Lin Yang, Tao Ni, Jian Zhang, Wei-Ping Deng
Summary: The development of efficient methods for synthesizing chiral polycyclic indoles is crucial for their wide applications in medicines, pesticides, and other functional molecules. The study revealed novel indolyl substituted metal-allyl zwitterionic intermediates that could participate in asymmetric cycloaddition reactions with high selectivities, leading to the synthesis of diverse chiral polycyclic indoles.
SCIENCE CHINA-CHEMISTRY
(2021)
Article
Clinical Neurology
Yuwen Cao, Jingying Wu, Yunhua Yue, Chao Zhang, Shihua Liu, Ping Zhong, Shige Wang, Xiaojun Huang, Weiping Deng, Jing Pan, Lan Zheng, Qing Liu, Liang Shang, Benyan Zhang, Jie Yang, Guang Chen, Shufen Chen, Li Cao, Xinghua Luan
Summary: NIID is a heterogeneous neurodegenerative disease with multiple clinical subtypes. The clinical features of Chinese NIID patients include variable onset age and disease duration, with common phenotypes such as tremor, dementia, and paroxysmal encephalopathy. Pathological examinations combined with genetic testing are the gold standard for diagnosis, and the involvement of lysosomal and mitochondrial dysfunction in the pathogenesis of NIID warrants further study.
ACTA NEUROLOGICA BELGICA
(2022)
Article
Chemistry, Multidisciplinary
Jian Zhang, Wu-Lin Yang, Hanliang Zheng, Yi Wang, Wei-Ping Deng
Summary: This study reports an unprecedented asymmetric gamma-allylic alkylation method using the Sc/Ir dual catalysis system, which provides synthetically versatile gamma-allylic crotonaldehydes with high efficiency and excellent selectivities. The dienolates, without essential auxiliary groups, are generated in situ through scandium triflate-mediated Meinwald rearrangement in an atom-economical manner. A Sc/Ir bimetallic catalytic cycle is proposed to explain the reaction mechanism using computational density functional theory calculations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Wu-Lin Yang, Xin-Yu Shang, Xiaoyan Luo, Wei-Ping Deng
Summary: The enantioselective cascade reaction between racemic 2-(1-hydroxyallyl)phenols and alkynols/alkynamides was achieved using a gold and iridium sequential catalytic system. This method provides efficient access to spiroketals and spiroaminals with excellent enantioselectivities. The synthetic utility of this method has been demonstrated by the enantioselective synthesis of an analogue of Paecilospirone.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Multidisciplinary
Tian Tan, Wei Wang, Kai Zhang, Zixiang Zhan, Weiping Deng, Qinghong Zhang, Ye Wang
Summary: Plastics play important roles in modern society, but their landfilling and discarding as waste contribute to environmental pollution and carbon loss, posing high risks to ecosystems and human health. Current physical recycling methods are limited to thermoplastic recycling and suffer from quality deterioration. Catalytic upcycling has emerged as a promising strategy to treat plastic waste by upgrading it into value-added products under mild conditions. This review highlights recent advances in the development of efficient heterogeneous catalysts and useful strategies for upcycling plastics into various valuable chemicals and materials.
Article
Chemistry, Organic
Fu-Sheng He, Ping Bao, Zhimei Tang, Feiyan Yu, Wei-Ping Deng, Jie Wu
Summary: This research developed a new photoredox-catalyzed reaction method, which can introduce various functionalized sulfonyl groups into ketones through the synthesis of easily accessible starting materials and good functional group compatibility. In addition, it is the first time that α-methylsulfonated ketones have been synthesized using methanol as the methyl source, which is an important industrial raw material.
Article
Clinical Neurology
Yang Gao, Weiping Deng, Jialan Sun, Dongqi Yue, Bei Zhang, Yulan Feng, Jun Han, Fanxia Shen, Jin Hu, Yi Fu
Summary: This study aimed to explore the association of dipping patterns and other factors with lacunes and enlarged perivascular spaces (EPVS) in patients with hypertension. The results showed that nocturnal blood pressure decline was negatively correlated with lacunes and EPVS, while mean systolic blood pressure level was positively correlated with them.
FRONTIERS IN NEUROLOGY
(2022)
Article
Chemistry, Multidisciplinary
Wu-Lin Yang, Xin-Yu Shang, Tao Ni, Hui Yan, Xiaoyan Luo, Hanliang Zheng, Zhong Li, Wei-Ping Deng
Summary: In this study, an efficient iridium/silver/acid ternary catalytic system was developed for the synthesis of bisbenzannulated [6,6]-spiroketals and [6,6]-spiroaminals with high diastereo- and enantioselectivities. The reaction mechanism and stereochemistry were elucidated through experimental studies and theoretical calculations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Physical
Jun Feng, Sha Xu, Hao Du, Qiaobin Gong, Shunji Xie, Weiping Deng, Qinghong Zhang, Ye Wang
Summary: This paper discusses the recent advances in the photocatalytic conversion of methanol into high-value chemicals, highlighting the differences between photocatalysis and thermocatalysis, as well as the key factors influencing catalytic performance. The challenges and opportunities of methanol conversion are also explored.
MOLECULAR CATALYSIS
(2022)
Article
Chemistry, Applied
Kai Zhang, ZiXiang Zhan, Minzhi Zhu, Haiwei Lai, Xiangyang He, Weiping Deng, Qinghong Zhang, Ye Wang
Summary: This article introduces an efficient electrocatalytic system using nickel oxide (NiO) and TEMPO or ACT as catalysts, which selectively oxidize key bio-platform molecules such as glucose, xylose, and 5-hydroxymethylfurfural (HMF) into corresponding dicarboxylic acids. NiO catalyzes the oxidation of aldehyde to carboxylic acid, while TEMPO or ACT oxidizes primary alcohol to aldehyde. The combination of NiO and TEMPO or ACT significantly accelerates the tandem oxidation of aldehyde and hydroxyl groups, achieving excellent yields (83%-99%) of dicarboxylic acids. Moreover, the combination catalyst enables the selective oxidation of glucose and xylose with high concentrations, offering a promising strategy for biomass valorization.
JOURNAL OF ENERGY CHEMISTRY
(2023)
Editorial Material
Chemistry, Applied
Weiping Deng, Ye Wang
JOURNAL OF ENERGY CHEMISTRY
(2023)
Article
Chemistry, Organic
Wenqi Liu, Meng Zang, Jian Zhang, Quannan Wang, Yang-Zi Liu, Wei-Ping Deng
Summary: An efficient method for the construction of 1,5-di/ox-azonanes via Pd-catalyzed [5 + 4] cycloaddition has been developed. This reaction demonstrates a high tolerance towards various functional groups and shows exclusive regioselectivity, resulting in a series of nine-membered heterocycles in moderate to excellent yields. The synthetic utility of the method has been further demonstrated by a gram-scale reaction.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Tao Ye, Fangyuan Cheng, Jian Zhang, Yang-Zi Liu, Quannan Wang, Wei-Ping Deng
Summary: In this paper, a palladium-catalyzed C-H carbonylation reaction of gem-disubstituted ethylenes with phenyl formate as a convenient CO surrogate is reported. The reaction proceeds through an aryl to vinyl 1,4-palladium migration, providing a wide range of beta, beta-diaryl substituted alpha, beta-unsaturated esters with high efficiency and excellent regio- and stereoselectivities. The synthetic protocol presented in this study offers a convenient and powerful method to directly access a key intermediate for (Z)-tamoxifen.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Review
Chemistry, Organic
Zhang Jian, Chen Ying, Wang Quannan, Shen Jiahuan, Liu Yangzi, Deng Weiping
Summary: The article introduces the asymmetric synthesis of chiral heterocyclic compounds using transition metal-catalyzed cyclization, focusing on the application and issues of allyl or propargyl heteroatom-dipole precursors.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Physical
Wei Wang, Yao Wang, Zixiang Zhan, Tian Tan, Weiping Deng, Qinghong Zhang, Ye Wang
Summary: This review article focuses on the selective deoxygenation of cellulose and its derived platforms such as glucose and 5-hydroxymethyl furfural (HMF) to produce valuable chemicals. The review highlights recent progress made in this area and discusses efficient catalytic systems and reaction mechanisms. The knowledge gained from this research can contribute to the rational design of effective strategies and catalysts for the utilization of lignocellulosic biomass in the future.
ACTA PHYSICO-CHIMICA SINICA
(2022)
Article
Chemistry, Organic
Wu-Lin Yang, Jia-Huan Shen, Zeng-Hui Zhao, Zhongao Wang, Wei-Ping Deng
Summary: In this study, a gold/palladium bimetallic relay catalytic strategy was developed for the synthesis of furan-fused azepines with excellent enantioselectivities. Enynamides were activated by a gold catalyst to generate azadienes in situ, which then reacted with Pd-TMM via the asymmetric [4 + 3] cycloaddition process. Furthermore, oxidative furan cleavage of the cycloadducts mediated by potassium nitrate allowed the synthesis of poly-functionalized enantioenriched azepines under mild conditions.
ORGANIC CHEMISTRY FRONTIERS
(2022)
