Article
Chemistry, Multidisciplinary
Hayato Nakagawa, Haruhiko Fuwa
Summary: Stereodivergent synthesis of 2,5-disubstituted pyrrolidines was achieved through a Au-catalyzed tandem intramolecular alkyne hydroamination/iminium formation/Et3SiH reduction. The stereochemical outcome could be switched by selecting an appropriate nitrogen protecting group. Total synthesis of a diastereomeric pair of alkaloid natural products, monomorine I and indolizidine 195B, was successfully accomplished to demonstrate the synthetic utility of the tandem reaction.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Jinping Yuan, Pankaj Jain, Jon C. Antilla
Summary: The catalytic asymmetric addition of beta,gamma-substituted allylboronates to aldehydes has been described, showing highly efficient and selective reactions.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Victor Garcia-Vazquez, Pablo Martinez-Pardo, Alexandru Postole, A. Ken Inge, Belen Martin-Matute
Summary: This study developed a method for synthesizing chiral trifluoromethylated aliphatic amines, which involves organocatalytic isomerization and imine/enamine reduction to obtain compounds with two noncontiguous stereogenic centers in high yields and selectivities. The method is effective for primary amine substrates and provides a new pathway for synthesizing chiral trifluoromethylated scaffolds.
Article
Multidisciplinary Sciences
Jie Wang, Wei-Feng Zheng, Xue Zhang, Hui Qian, Shengming Ma
Summary: This study reports the synthesis of non-readily available enantioenriched tetrasubstituted allenes through rhodium-catalyzed reactions controlled by steric hindrance. Detailed mechanistic experiments and density functional theory studies reveal the mechanism behind the formation of different stereochemistry under different reaction conditions. A stereodivergent protocol to construct the enantiomer of optically active tetrasubstituted allenes from the same starting materials is successfully developed based on these mechanistic understandings.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Wenbo Ming, Xiaocui Liu, Lujia Mao, Xiao Gu, Qing Ye
Summary: This review article summarizes recent advances in transition-metal catalyzed preparation of chiral allylboronates, focusing on developments within the past three years and emphasizing asymmetric catalysis. The discussion is divided into substrate-controlled and catalyst-controlled synthesis based on mechanisms for achieving selectivity in terms of chemo-, regio-, stereo- and enantioselectivities.
CHINESE JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Organic
HtooTint Wai, Glenn C. Micalizio
Summary: Efforts to establish an asymmetric entry to hexanorlanostanes resulted in a concise synthesis of 7,11-dideoxy-Delta 5-lucidadone H from epichlorohydrin. By utilizing metallacycle-mediated annulative cross-coupling and stereoselective formation, key transformations were achieved, including the inversion of the C13 quaternary center and Lewis acid mediated rearrangement, leading to the generation of a hexanorlanostane system.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Minghui Zhu, Qinglong Zhang, Weiwei Zi
Summary: The study presents a dual-metal catalyzed diastereodivergent coupling method for the synthesis of beta-amino alcohols with multiple stereoisomers, enabling the concise preparation of natural products such as mycestericins F and G.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Jialin Qi, Fang Wei, Shuai Huang, Chen-Ho Tung, Zhenghu Xu
Summary: A new method has been developed for the synthesis of sulfur-containing chiral beta-lactams with two consecutive stereogenic centers using copper(I)-catalyzed asymmetric, three-component interrupted Kinugasa reaction. The key lies in the interception of in situ formed chiral four membered copper(I) enolate intermediate with sulfur electrophiles, resulting in good yields and excellent diastereo- and enantioselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Xue-Song Gu, Ying Xiong, Fan Yang, Na Yu, Pu-Cha Yan, Jian-Hua Xie, Qi-Lin Zhou
Summary: An iridium-catalyzed asymmetric hydrogenation method involving dynamic kinetic resolution was successfully developed using chiral spiro PNN-ligands containing a C5-substituted chiral oxazoline unit. This protocol, combined with simple dehydration, provides a straightforward approach to prepare enantiomerically enriched 3-aryloxy tetrahydrofurans, which are prevalent structural motifs in many approved drugs and clinical candidates.
Article
Chemistry, Multidisciplinary
Li Ling, Zeli Song, He Shan, Chao Wang, Shouting Li, Yanjiao Wang, Jianfeng Hu, Qian Chen, Hao Zhang, Yong Yang
Summary: A series of planar chiral indene-fused ferrocenes were successfully synthesized with excellent yields (up to 99%) and high enantioselectivities (up to 99% ee) through intramolecular asymmetric C-H arylation. These compounds were then transformed to chiral ferrocenyl phosphines, featuring both planar and central chiralities, in good yields (up to 83%) and excellent diastereoselectivities (up to 99% de) through diastereoselective phosphination. The newly developed ligands demonstrated potential applications in a Pd-catalyzed enantioselective allylic alkylation reaction with high enantioselectivity (92% ee) and good yield (89%).
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Applied
Mattia Lazzarotto, Peter Hartmann, Jakob Pletz, Ferdinand Belaj, Wolfgang Kroutil, Stefan E. Payer, Michael Fuchs
Summary: The substrate scope of the asymmetric allylation catalyzed by TRIP has been expanded to include non-cyclic ester organozinc reagents and ketones, resulting in high yields and significant changes in stereoselectivity of the products.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Peng Zou, Hongjian Yang, Jian Wei, Taimin Wang, Hongbin Zhai
Summary: The first asymmetric total synthesis of three picrinine-type akuammiline alkaloids has been achieved, involving an efficient acid-promoted oxo-bridge ring-opening, an unusual Dauben-Michno oxidation, and a nickel-mediated reductive Heck reaction to forge the [3.3.1]-azabicyclic core.
Article
Chemistry, Organic
Tao Zhang, Wen-Ao Li, Hong-Cheng Shen, Shu-Sen Chen, Zhi-Yong Han
Summary: An asymmetric Heck-Matsuda reaction targeting acyclic internal alkenes was successfully developed through the strategy of chiral anion phase transfer, resulting in high levels of enantioselectivity in the formation of chiral ketones. The use of a catalytic amount of dimethyl sulfoxide (DMSO) as an additive is crucial for suppressing palladium-hydride-mediated side reactions.
Article
Chemistry, Multidisciplinary
Yi-Wen Xie, Zhen-Ni Zhao, Zi-Wei Lin, Yu-Hao Wang, Ya-Qun Liu, Yi-Yong Huang
Summary: The Petasis reaction successfully synthesized alpha- and beta-butadienyl amines using (1S,2R)-1-amino-2-indanol as the substrate, demonstrating metal-free nature, broad substrate scope, complete regioselectivities, and high to excellent chirality induction. The favored nucleophilic addition across the Si-face of the imine intermediate was explained using DFT calculations of the six-membered chair-like transition state.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Lei Yang, Wen-Qiang Xu, Tao Liu, Yichen Wu, Biqin Wang, Peng Wang
Summary: The synthesis of a Si-centered spirocyclic skeleton, SPOSiOL, and its derived chiral ligands were reported in this study, showcasing their potential in transition metal-catalyzed asymmetric reactions. This finding emphasizes the value of Si-centered spirocyclic scaffolds in asymmetric catalysis.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Jin Lin, Fang Wang, Jing Tian, Jisheng Zhang, Yong Wang, Wei Sun
Summary: The enantioselective epoxidation of olefin by Mn-II(R,R-PMCP)(OTf)(2), H2O2 and H2SO4 was studied using DFT calculations and experiments. Theoretical results suggest that [Mn-V(O)(R,R-PMCP)(SO4)](+) species acts as the active species for the olefin epoxidation, which is formed with the assistance of H2SO4. Mn-III-persulfate also plays a role in this system but does not directly promote the olefin epoxidation, instead transforming into Mn-V(O) species.
CHINESE CHEMICAL LETTERS
(2022)
Article
Chemistry, Physical
Lixian Wang, Jin Lin, Qiangsheng Sun, Chungu Xia, Wei Sun
Summary: A series of Mn(I) catalysts with chiral bidentate benzimidazoles derived from easily available amino acids have been developed for asymmetric transfer hydrogenation (ATH), showing high activity and enantioselectivity. These phosphine-free chiral Mn catalysts can efficiently convert bulky substrates into drug intermediate alcohols, with a possible mechanism and enantiocontrol model proposed based on experimental and DFT studies.
Article
Chemistry, Applied
Jing Tian, Jin Lin, Jisheng Zhang, Chungu Xia, Wei Sun
Summary: A family of manganese complexes derived from L-proline has been synthesized and characterized, showing different catalytic activities and enantioselectivities depending on the R group on the diamine backbone. Experimental results indicate that isopropyl substitution on the (R)peb ligand affects the catalytic reaction and prevents the use of H2O2 as an oxidant.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Lixian Wang, Jin Lin, Chungu Xia, Wei Sun
Summary: An asymmetric transfer hydrogenation (ATH) of quinolines has been developed in water or biphasic systems, utilizing a water-soluble iridium catalyst with an easily available aminobenzimidazole ligand. The reaction proceeds smoothly with a catalyst loading as low as 0.001 mol%, achieving high turnover numbers and turnover frequencies. Various quinoline and N-heteroaryl compounds can be transformed into the desired products with high yield and enantiomeric excess.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Qiaowen Liu, Feng Han, Hongfeng Zhuang, Tong Zhang, Na Ji, Chengxia Miao
Summary: Direct metal-free deoxygenation of highly active allylic alcohols was achieved through catalysis by a Bronsted acid, avoiding tedious reaction steps and metal contamination. The system was found to be mainly suitable for aromatic allylic alcohols, with excellent yields obtained via gram-scale synthesis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Qiaowen Liu, Feng Han, Hongfeng Zhuang, Zenghong Song, Jian Zhang, Tong Zhang, Ning Wang, Chengxia Miao
Summary: In this study, a metal-free and recyclable catalytic system using pyrrolidine-based ionic liquids as catalysts for direct reduction of aromatic allylic alcohol was developed. The use of dimethyl carbonate as the solvent not only acted as a green solvent but also stabilized the reaction intermediates and improved the reactivities. The method showed high yield, scalability, and environmental friendliness.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2022)
Article
Chemistry, Physical
Huimin Qi, Daqian Xu, Jin Lin, Wei Sun
Summary: In this study, copper(II) complexes bearing different ligands were prepared, and it was found that the copper(II)-N4 complex can efficiently catalyze the hydroxylation of benzene, achieving a certain yield. In comparison, copper(II) complexes supported by other ligands showed inferior performance in this reaction.
MOLECULAR CATALYSIS
(2022)
Article
Chemistry, Applied
Jing Tian, Daqian Xu, Wei Sun
Summary: Several cobalt(II) complexes supported by tetradentate and tridentate ligands have been prepared and characterized. X-ray crystallographic analysis shows that the cobalt complex of the BPMB ligand has a distorted octahedral configuration. These complexes can catalyze the transfer hydrogenation reaction of simple olefins with good to excellent yields, and the Co-N4 complexes are more effective than the Co-N3 complex.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Haotian Lv, Feng Han, Ning Wang, Nan Lu, Zenghong Song, Jian Zhang, Chengxia Miao
Summary: A convenient and environmentally friendly method using acidic ionic liquid as a metal-free catalyst and dimethyl carbonate as a green solvent has been demonstrated for the synthesis of polysubstituted olefins, avoiding the use of toxic solvents and additives and reducing waste production through the construction of new C-C bonds.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Ning Wang, Zengmin Li, Qin Hou, Feng Han, Yucai Yan, Jian Zhang, Chengxia Miao
Summary: Sulfonic acid-functionalized ionic liquid was used as a catalyst for the alkylation and cyclization of 4-hydroxycoumarin derivatives, showing adjustable and recyclable properties. The developed metal-free catalytic systems allow for smooth gram-scale reactions.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Physical
Huimin Qi, Lixian Wang, Qiangsheng Sun, Wei Sun
Summary: This article describes a stable iridium catalyst with a chiral 2-pyridyl imidazoline ligand for the asymmetric transfer hydrogenation (ATH) of quinolines and N-heteroaryl compounds. The ATH system uses formic acid as the hydrogen source and water as the solvent. Various quinolines and N-heteroaryl compounds can be efficiently converted into desired products with moderate to good enantioselectivity at a catalyst loading as low as 0.001 mol% under mild conditions.
MOLECULAR CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Hongfeng Zhuang, Qin Hou, Feng Han, Haotian Lv, Chengxia Miao
Summary: This study established a simple catalytic system for the O-alkylation of oximes with alcohols using H3PW12O40 as the catalyst and dimethyl carbonate as the solvent. The system simplified the reaction systems, realized catalytic transformation, and improved the yields and selectivities.
Article
Chemistry, Physical
Bingyang Wang, Lixian Wang, Jin Lin, Chungu Xia, Wei Sun
Summary: A series of zinc complexes with tetradentate aminopyridine ligands were synthesized and characterized. These zinc catalysts were able to couple CO2 with epoxides in excellent yields and broad substrate scope under solvent- and cocatalyst-free conditions. The catalysts could be easily recovered and reused without significant loss in catalytic activity. Catalyst Zn-3 was found to be multifunctional due to a Lewis acidic zinc center, a nucleophilic halide anion, and the release of a pyridine molecule for CO2 activation.
Article
Chemistry, Multidisciplinary
Xin Zhou, Zhaozhan Wang, Bo Yu, Shaoping Kuang, Wei Sun, Yong Yang
Summary: This study presents a highly efficient method for synthesizing amides using a soluble heterogeneous Pd catalyst, which enables the hydroaminocarbonylation of alkenes and alkynes with amines and CO gas. The new method provides high yields and a broad substrate scope, as well as excellent stability and reusability of the catalyst.
Article
Chemistry, Multidisciplinary
Jin Lin, Qiangsheng Sun, Wei Sun
Summary: The hydroxylation of hexane by two (FeO)-O-IV complexes with pentadentate and tetradentate ligands derived from l-proline was studied using DFT calculations, which showed that both complexes have triplet ground states. The hydrogen atom abstraction processes by both species proceed through a two-state reactivity, indicating that HAA occurs via a low-barrier quintet surface. Additionally, beyond the rebound step, the dissociation path after HAA was also calculated to potentially occur.
Review
Chemistry, Multidisciplinary
Dan He, Yawen Li, Fuwen Zhao, Yuze Lin
Summary: High trap density in organic solar cells leads to localized charge carriers and reduced carrier lifetime, limiting device efficiency. This feature article summarizes the recent advances of trap suppression by material design and device engineering.
CHEMICAL COMMUNICATIONS
(2024)
Review
Chemistry, Multidisciplinary
Olivier Monfort, Arshitha Madhusudhan, Martin Motola
Summary: This article presents the advantages of coupling photocatalysis and Fenton-based processes for environmental remediation and discusses their synergy. It critically examines the simultaneous triggering of these two processes and provides insights into research approaches. The study aims to enhance understanding of this complex process and highlight the potential integration of new catalysts in current wastewater treatment technology.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Manideepa Dhar, Chittaranjan Mishra, Avijit Das, Uttam Manna
Summary: An approach of 'polymerization of monomers in its aggregated form' has been introduced to tailor the water wettability of fibrous and porous substrates, achieving hydrophobicity to superhydrophobicity transition, as well as patterned wettability. This facile chemical method provides a durable coating with adjustable and patterned wettability for various potential applications.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Saswat Ranjan Bhoi, Chhanda Debnath, Shikha Gandhi
Summary: In this article, a novel catalytic reaction using Pd(0) and Bronsted acid is reported for the synthesis of biologically important imidazolidinone-fused N-heterocycles through redox-neutral intramolecular N-allylation of indoles and pyrroles with alkynes. This atom-economical method is applicable to a wide range of substrates and eliminates the need for leaving groups or oxidizing agents commonly used in traditional allylation reactions.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Longkun Chen, Mingshuai Zhang, Meichen Liu, Zhuoyuan Liu, Yuetong Qiu, Zhilai Zhang, Fuchao Yu, Jiuzhong Huang
Summary: In this study, an efficient Rh(III)-catalyzed selective mono- and dual-C-H bond functionalization/cyclization with iodonium ylide as the sole coupling partner was demonstrated. Fused benzodiazepine skeletons were obtained in excellent yields, providing an improved approach to dual C-H unsymmetrical functionalization.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Alice Kennett, Sven Epple, Gabriella van der Valk, Irene Georgiou, Evelyne Gout, Romain R. Vives, Angela J. Russell
Summary: This study presents the design and synthesis of sulfated disaccharide inhibitors based on IdoA(2S)-GlcNS(6S), which showed potent inhibition of Sulf-2. The results suggest that IdoA(2S)-GlcNS(6S) is the shortest fragment size required for effective inhibition of Sulfs, and a trisulfated disaccharide is identified as the minimal fragment size of heparan sulfate for effective endosulfatase inhibition.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Mauro Garbini, Andrea Brunetti, Riccardo Pedrazzani, Magda Monari, Massimo Marcaccio, Giulio Bertuzzi, Marco Bandini
Summary: The self-adaptability of galvanostatic electrolysis was found to be helpful in a multistage chemo- and diastereoselective electrochemically promoted cyclodimerization of chalcones. Through a series of reductive events, densely functionalized cyclopentanes with five contiguous stereocenters were obtained (25 examples, yields up to 95%, dr values up to >20:1). Further experimental and electrochemical investigations indicated the crucial role of dynamic kinetic resolution of the aldol intermediate in the reaction mechanism.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Dhananjay S. Nipate, Neha Meena, Prakash N. Swami, Krishnan Rangan, Anil Kumar
Summary: In this study, the synthesis of functionalized benzo[a]phenazines and indazolo[2,3-a]quinolines was achieved through Rh(III)-catalyzed oxidative annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols. The method showed a wide substrate scope, excellent functional group tolerance, good to high yields of annulated products, and the capability for scaled-up synthesis. A tentative mechanism of the annulation reaction was proposed based on a preliminary mechanistic investigation.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Ruonan Zhang, Abudukadi Tudi, Xia Yang, Xuping Wang, Zhihua Yang, Shujuan Han, Shilie Pan
Summary: A new lead tellurium borate material with a unique fundamental building block [B4O10] was synthesized and found to exhibit high birefringence. The structure-property relationship was discussed using first-principles calculations.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Amresh Kumar Singh, Baishali Thakurta, Anupam Giri, Monalisa Pal
Summary: This study introduces three key concepts for the quick synthesis of large-scale high-quality 2D materials films and their utilization in device fabrication.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Reina Hagiwara, Shun Nishimura, Kosuke Okeyoshi
Summary: A copolymer-conjugated nanocatalytic system has been developed to improve electron transfer and enhance photoinduced H2 generation.
CHEMICAL COMMUNICATIONS
(2024)
