Article
Chemistry, Physical
Ying Yang, Nan-Nan Hang, Hui-Yao Liu, Shufeng Chen, Jialin Ming
Summary: One-step asymmetric synthesis of metallocenes with planar and central chirality was achieved using rhodium catalysis. The reactions proceeded through a desymmetric conjugate addition-Michael cyclization sequence, allowing for the simultaneous construction of both planar and central chirality. The synthetic utility of this method was demonstrated by the asymmetric synthesis of a novel chiral chain diene ligand.
Article
Chemistry, Organic
Tian-Yuan Zhao, Ke Li, Liang-Liang Yang, Shou-Fei Zhu, Qi-Lin Zhou
Summary: The highly enantioselective and diastereoselective nickel-catalyzed desymmetrizing cyclization of 1,6-dienes using chiral spiro phosphoramidite ligands provides a new atom- and step-economic approach to chiral spiro lactones and analogues bearing a quaternary stereo-center, which holds significant synthetic application value.
Article
Chemistry, Multidisciplinary
Wenpeng Ma, Li-Chuan Liu, Kun An, Tao He, Wei He
Summary: A Rh-catalyzed desymmetrization of dihydrosilanes under simple and mild conditions provides easy access to a range of chiral monohydrosilanes with good yields and excellent enantioselectivities (up to >99% ee). These monohydrosilanes serve as a useful platform to access stereogenic silicon compounds and probe silicon stereochemistry.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Physical
Irene Sanchez-Sordo, Andrea Chaves-Pouso, Jaime Mateos-Gil, Eva Rivera-Chao, Martin Fananas-Mastral
Summary: In this study, a new copper-catalyzed coupling reaction is reported for the enantioselective desymmetrization of chiral cycloalkenes. The method allows for the synthesis of chiral products with high regio-, diastereo-, and enantioselectivity, which can serve as versatile building blocks for the synthesis of various optically active cyclic compounds.
Article
Chemistry, Multidisciplinary
F. Wieland Goetzke, Alexander M. L. Hell, Lucy van Dijk, Stephen P. Fletcher
Summary: The study describes an asymmetric cross-coupling reaction between cyclobutenes and arylboronic acids initiated by Rh-catalyzed asymmetric carbometallation. This method allows for the synthesis of highly stereoselective cyclobutane derivatives and demonstrates wide applicability in drug synthesis.
Article
Chemistry, Applied
Yuya Kaieda, Kosuke Yamamoto, Masami Kuriyama, Osamu Onomura
Summary: A rhodium-catalyzed reaction has been developed to convert N-sulfonyl-1,2,3-triazoles and carboxylic esters into 2,5-disubstituted oxazole derivatives under mild reaction conditions.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Liher Prieto, Efraim Reyes, Uxue Uria, Luisa Carrillo, Jose L. Vicario
Summary: This work presents the desymmetrization of oxabenzonorbornadienes through the (3+2) cycloaddition reaction with hydrazones using a chiral Bronsted acid catalyst. The reaction proceeds via the activation of the hydrazone by the chiral acid catalyst, which reacts with the olefinic counterpart in a (3+2) fashion. Under optimized conditions, the reaction selectively produces exo cycloaddition products with moderate stereoselectivities. The scope of the reaction is explored with 21 examples of highly functionalized tetrahydroepoxybenzoindazole compounds.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Qijian Ni, Zhiming Zhu, Yanjun Fan, Xiaoyun Chen, Xiaoxiao Song
Summary: The research has successfully developed an organocatalytic highly diastero- and enantioselective Friedel-Crafts conjugate addition method for adding indolizines to cyclopentenediones to obtain the desired products. The utility of the method was demonstrated through various late-stage functionalizations.
Article
Multidisciplinary Sciences
Jia-Lei Yan, Rakesh Maiti, Shi-Chao Ren, Weiyi Tian, Tingting Li, Jun Xu, Bivas Mondal, Zhichao Jin, Yonggui Robin Chi
Summary: In this study, a chiral solution utilizing N-heterocyclic carbene (NHC) catalyst was developed for the preparation of axially chiral styrenes with high enantioselectivity and excellent yields. The sulfone and carboxylic ester moieties in the styrenes are common functional groups in bioactive molecules and asymmetric catalysis.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Binmiao Yang, Jun Dai, Yixin Luo, Kai Kiat Lau, Yu Lan, Zhihui Shao, Yu Zhao
Summary: This method achieves an unprecedented desymmetrization of meso 1,3-diones by enantioselective intermolecular condensation, producing cyclic and acyclic keto-hydrazones with an all-carbon quaternary center in high efficiency and enantioselectivity. The compounds are versatile for preparing multifunctional building blocks and heterocycles with excellent stereoselectivity.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Multidisciplinary Sciences
Qingjing Yang, Zihao Wang, Catherine Hong Huan Hor, Haitao Xiao, Zhaoxiang Bian, Jun (Joelle) Wang
Summary: This study reports a highly efficient kinetic resolution method for the synthesis of chiral flavanols with two stereocenters. In vitro experiments and RNA sequencing analysis revealed the potential anti-inflammation effects of these flavanols.
Article
Chemistry, Multidisciplinary
Yi-Xuan Ding, Zhou-Hao Zhu, Mu-Wang Chen, Chang-Bin Yu, Yong-Gui Zhou
Summary: In this study, the asymmetric hydrogenation of all-carbon aromatic rings was achieved using rhodium/diphosphine catalysts. The introduction of chiral diphosphine ligands with steric hindrance and strong electron-donating properties was key to the success in obtaining axially chiral cyclic compounds with high enantioselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Bingxian Liu, Pengfei Xie, Jie Zhao, Juanjuan Wang, Manman Wang, Yuqin Jiang, Junbiao Chang, Xingwei Li
Summary: Desymmetrization of gem-dimethyl groups en route to the rhodium(III)-catalyzed enantioselective sp(3) C-H amidation leads to the synthesis of synthetically important beta-amino alcohol derivatives in moderate to good yields and high enantioselectivity. The high enantioselectivity is achieved through the use of an appropriate oxime directing group, sterically biased gem-groups in the C-H substrate, and the high reactivity of the amidating reagent.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Xingwei Li, Heng Song, Songjie Yu, Ruijie Mi, Xiao-Xi Li
Summary: The incorporation of fluorine atoms in organics improves their bioactivity and lipophilicity. Catalytic functionalization of gem-difluorodienes represents one of the most straightforward approaches to access fluorinated alkenes. Our asymmetric protocol exhibits high 1,4-regio- and enantioselectivity with utility in the late-stage modification of pharmaceuticals and natural products. Stoichiometric experiments provide evidences for the π-allylrhodium pathway. Related oxyamination was also realized when trifluoroethanol was used as an oxygen nucleophile.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Shuailong Li, Dequan Zhang, Runtong Zhang, Shao-Tao Bai, Xumu Zhang
Summary: This article reports a novel rhodium catalyst that enables highly efficient and selective hydroformylation of cyclopropyl-functionalized trisubstituted alkenes, resulting in valuable chiral cyclopropyl entities. The modified ligand used in this study exhibits superior performance compared to traditional diphosphine ligands in asymmetric catalysis. Gram-scale reactions and subsequent transformations of the products were also demonstrated.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
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)