Article
Chemistry, Organic
Zhehui Liao, Jiantao Zhang, Tongxiang Cao, Shifa Zhu
Summary: A series of highly strained bicyclo[3.n.1]alkenones have been successfully synthesized with good-to-excellent enantioselectivities and moderate-to-good yields via copper-catalyzed formal [3+3] cycloaddition. The versatile chiral cycloadducts could be selectively converted into various valuable bridge systems, showing great potential for the construction of natural and bioactive compounds containing a [3.n.1] moiety.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Luo-Yu Wang, Jiapei Miao, Yu Zhao, Bin-Miao Yang
Summary: We report a highly selective abbreviation for the efficient synthesis of 1,1'-biheteroaryls. Under the cooperative catalysis of chiral phosphoric acid and InBr3, reactions between 2,3-diketoesters and 1,3-dione-derived enamines resulted in the highly enantioselective construction of 1,1'-pyrrole-indoles with up to 92% yield and 94% enantiomeric excess. Derivatizations of these compounds to diverse functionalized N-N linked axially chiral biheteroaryls have also been demonstrated.
Article
Chemistry, Organic
Luo-Yu Wang, Jiapei Miao, Yu Zhao, Bin-Miao Yang
Summary: We developed a highly selective method for synthesizing 1,1'-biheteroaryls bearing a chiral N-N axis. By using chiral phosphoric acid and InBr3 as cooperative catalysts, 2,3-diketoesters reacted with 1,3-dione-derived enamines to construct 1,1'-pyrrole-indoles with high enantioselectivity, up to 92% yield, and up to 94% enantiomeric excess (ee), or bisindoles with up to 92% ee. Derivatizations of these compounds resulted in diverse functionalized N-N linked axially chiral biheteroaryls.
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, Organic
Xinghua Wang, Shi-Jun Li, Ya-Nan Wang, Donghui Wei, Yu Lan
Summary: Desymmetrizing reactions of olefins catalyzed by N-Heterocyclic carbene (NHC) have been rapidly developing, but the origins of the chemo- and stereoselectivities in these reactions are still poorly understood. This study proposes a mechanistic map to predict how these selectivities are controlled by different active intermediates and contradicts a previous proposition regarding the determination of product structures by a transformation between a pair of isomers.
Article
Chemistry, Multidisciplinary
Xiongfei Deng, Shiqi Zhang, Hesen Huang, Xin Cui, Zhuo Tang, Guangxun Li
Summary: Highly enantioselective sulfa-Michael additions between 2-alkenyl quinoxalines and aromatic thiols were achieved using a low loading of chiral phosphoric acid catalyst. The investigation revealed that the two C = N units of quinoxalines are essential for controlling the enantioselectivities. Substituted non-terminal 2-alkenes with aryls or alkyls, and even other electro-withdrawing groups like ketones, esters, or amides, selectively reacted and yielded the desired products with good regioselectivities, high yields, and good ee values.
CHINESE CHEMICAL LETTERS
(2023)
Article
Chemistry, Organic
Jixin Pian, Qingqing Chen, Yujiao Luo, Zhifei Zhao, Jichang Liu, Lin He, Shi-Wu Li
Summary: An enantioselective cyclopropanation reaction of sulfoxonium ylides with beta,gamma-unsaturated ketoesters catalyzed by a chiral rhodium catalyst has been achieved, leading to the synthesis of various optically pure cyclopropanes.
Article
Chemistry, Organic
Xuegang Fu, Yuting Yan, Hexin Sun, Siying Li, Jianhui Huang
Summary: In this study, a naturally occurring alkaloid called aloperine was used as a chiral skeleton for the development of new ligands/catalysts in asymmetric synthesis. The Pd-catalyzed asymmetric hydroarylation using these chiral 1,3-diamine ligands showed high yields and enantioselectivities, indicating their potential in organocatalysis. This discovery opens up new possibilities in the design and development of natural product-inspired chiral ligands.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Qian-Jin An, Wang Xia, Wei-Yi Ding, Huan-Huan Liu, Shao-Hua Xiang, Yong-Bin Wang, Guofu Zhong, Bin Tan
Summary: This study presents a strategy for the synthesis of axially chiral N-arylbenzimidazoles using chiral phosphoric acid catalysis, demonstrating excellent chemo- and regioselectivity as well as high levels of enantiocontrol. The nitroso group plays a unique role in the domino reaction, acting as a linchpin to facilitate C-N bond formation and oxidative aromatization. The resulting atropisomeric products can be further elaborated to produce axially chiral derivatives for potential applications in asymmetric catalysis.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Correction
Chemistry, Organic
Xabier del Corte, Edorta Martinez de Marigorta, Francisco Palacios, Javier Vicario, Aitor Maestro
Summary: This correction addresses the article by Xabier del Corte et al. on the applications of chiral phosphoric acid organocatalysts in enantioselective additions to CO and CN bonds, published in Org. Chem. Front., 2022, 9, 6331-6399.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Xue-Jiao Lv, Yong-Chao Ming, Hui-Chun Wu, Yan-Kai Liu
Summary: In this study, a Bronsted acid-catalyzed cascade acyclic N,O-hemiaminal formation/oxa-Michael reaction was developed for the synthesis of cis-2,6-disubstituted tetrahydropyrans bearing an exo amide group, namely cyclic N,O-aminals. Various different amides were applicable for the reaction sequence using TsOH, and enantioenriched cyclic N,O-aminal scaffolds were obtained by using chiral phosphoric acid. Mechanistic investigations revealed that the good enantioselectivity was attributed to a H2O controlled dynamic kinetic resolution of the in situ formed acyclic N,O-hemiaminal intermediate. Additionally, divergent transformations of the products resulted in various synthetically useful heterocyclic architectures.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Li-Xia Liu, Yu-Qing Bai, Xiang Li, Chang-Bin Yu, Yong-Gui Zhou
Summary: Combining base-promoted retro-sulfa-Michael addition with palladium-catalyzed asymmetric allenylic alkylation, a streamlined synthesis of chiral thiochromanones containing two central chiralities (including a quaternary stereogenic center) and an axial chirality (allene unit) was successfully achieved, with yields up to 98%, dr of 49.0:1, and >99% ee.
Article
Chemistry, Organic
Changkai Wang, Jiangtao Sun
Summary: An efficient method for the synthesis of bipyrroles with an axially chiral N-N bond has been developed using a rhodium-catalyzed C-H bond insertion reaction. The desired atropisomers were obtained in high yields (up to 97%) and with excellent enantioselectivities (up to 99% ee).
Article
Chemistry, Organic
Chun-Tai Hung, Chun-Wei Lu, Shi-Han Huang, Yin-Feng Lu, Hsiang-Chi Chou, Cheng-Che Tsai
Summary: This research utilizes chiral sulfinamides as nucleophiles in intramolecular allylic substitution and sequential aerobic oxidation with aza-Michael addition reactions, achieving good yields of chiral isoindolines and high diastereoselectivities.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Jinshan Li, Haohua Chen, Rong Zhong, Lei Zhu, Saimei Liu, Hanfeng Ding, Jianguo Yang, Lei Wang, Yu Lan, Zhiming Wang
Summary: A catalytic and highly enantioselective Mukaiyama-Michael addition of difluoroenoxysilanes to azadienes has been developed using perfluorinated aryl-incorporating chiral monophosphoric acid (PF-CPA) as an effective catalyst. The presence of perfluoroaryl substituents not only enhances catalytic activity but also creates a confined chiral environment for highly enantioselective transformations.
Article
Chemistry, Multidisciplinary
Somnath Narayan Karad, Heena Panchal, Christopher Clarke, William Lewis, Hon Wai Lam
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2018)
Article
Chemistry, Multidisciplinary
Thi Le Nhon Nguyen, Celia A. Incerti-Pradillos, William Lewis, Hon Wai Lam
CHEMICAL COMMUNICATIONS
(2018)
Article
Chemistry, Multidisciplinary
Yunfei Luo, Steven M. Wales, Stamatis E. Korkis, Iain D. Roy, William Lewis, Hon Wai Lam
CHEMISTRY-A EUROPEAN JOURNAL
(2018)
Article
Chemistry, Multidisciplinary
Johnathon D. Dooley, Hon Wai Lam
CHEMISTRY-A EUROPEAN JOURNAL
(2018)
Correction
Chemistry, Multidisciplinary
Alistair Groves, Jose I. Martinez, Joshua J. Smith, Hon Wai Lam
CHEMISTRY-A EUROPEAN JOURNAL
(2019)
Article
Chemistry, Multidisciplinary
Harley Green, Stephen P. Argent, Hon Wai Lam
Summary: This study describes a novel domino reaction involving nickel-catalyzed additions of (hetero)arylboronic acids to alkynes, followed by cyclization onto acyclic ketones to yield chiral tertiary-alcohol-containing products with high enantioselectivities. The reversible E/Z isomerization of the alkenylnickel intermediates allows overall anti-arylmetallative cyclization to occur, producing products with ring systems similar to certain diarylindolizidine alkaloids.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Review
Chemistry, Multidisciplinary
Simone M. Gillbard, Hon Wai Lam
Summary: The use of arylboron reagents in metal-catalyzed domino addition-cyclization reactions is an important synthetic strategy for the preparation of diverse, highly functionalized carbo- and heterocyclic products. Recent studies have shown that nickel catalysts offer unique reactivity and access to products that are otherwise difficult to obtain.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Luke O'Brien, Stephen P. Argent, Kristaps Ermanis, Hon Wai Lam
Summary: Gold(I)-catalyzed nucleophilic allylations of pyridinium and quinolinium ions with various allyl pinacolboronates were studied. The reactions showed high selectivity and provided a variety of functionalized 1,4-dihydropyridines and 1,4-dihydroquinolines. Experimental evidence and density functional theory calculations revealed the mechanistic insights.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Multidisciplinary
Dmitry Gorbachev, Elliot Smith, Stephen P. Argent, Graham N. Newton, Hon Wai Lam
Summary: This study describes the synthesis of new morphinan opioids by adding photochemically generated carbon-centered radicals to substrates containing an enone in the morphinan C-ring. By using tetrabutylammonium decatungstate (TBADT) as a hydrogen atom transfer photocatalyst, diverse radical donors can be used to prepare a variety of C8-functionalized morphinan opioids. This work demonstrates the feasibility of late-stage modification of complex, highly functionalized substrates.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Simone M. Gillbard, Harley Green, Stephen P. Argent, Hon Wai Lam
Summary: Enantioselective nickel-catalyzed reactions of (hetero)arylboronic acids or alkenylboronic acids with substrates containing an alkyne tethered to various acyclic electron-deficient alkenes are discussed in this study.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Alistair Groves, Jinwei Sun, Hal R. I. Parke, Michael Callingham, Stephen P. Argent, Laurence J. Taylor, Hon Wai Lam
Article
Chemistry, Multidisciplinary
Riccardo Di Sanza, Thi Le Nhon Nguyen, Naeem Iqbal, Stephen P. Argent, William Lewis, Hon Wai Lam
Article
Chemistry, Multidisciplinary
Luke O'Brien, Somnath Narayan Karad, William Lewis, Hon Wai Lam
CHEMICAL COMMUNICATIONS
(2019)
Article
Chemistry, Multidisciplinary
Rebecca E. Ruscoe, Michael Callingham, Joshua A. Baker, Stamatis E. Korkis, Hon Wai Lam
CHEMICAL COMMUNICATIONS
(2019)
Article
Chemistry, Multidisciplinary
Heena Panchal, Christopher Clarke, Charles Bell, Somnath Narayan Karad, William Lewis, Hon Wai Lam
CHEMICAL COMMUNICATIONS
(2018)
Article
Chemistry, Multidisciplinary
Alexander M. Prophet, Kritanjan Polley, Gary J. Van Berkel, David T. Limmer, Kevin R. Wilson
Summary: The oxidation kinetics of iodide by ozone at the air-water interface is studied in single microdroplets. Molecular simulations and kinetic modeling are used to understand the underlying multiphase mechanism.
Article
Chemistry, Multidisciplinary
Rong Zhang, Jiajing Lan, Fei Wang, Shumei Chen, Jian Zhang
Summary: By utilizing 1,1'-ferrocene dicarboxylic acid as a chelating and surface protection ligand, we have synthesized multi-nuclear indium oxide clusters with varying nuclear sizes, including heptanuclear and thirteen-nuclear clusters. These clusters possess labile coordination sites, allowing for structural modification and self-assembly, resulting in the formation of various cluster structures.
Article
Chemistry, Multidisciplinary
Hui Wang, Hui Liu, Mingsen Wang, Jiaheng Hou, Yongjun Li, Yuancheng Wang, Yingjie Zhao
Summary: Two supramolecular complexes were prepared using CBs and M1, and their single-crystal structures were analyzed by SCXRD. The unexpected 1:2 self-assembly structure between M1 and CB[8] was discovered for the first time. These complexes exhibit unique photophysical properties and provide valuable information about the structure and photophysical properties of supramolecular complexes.
Article
Chemistry, Multidisciplinary
Chang-Hee Lee, Sookil Park, Sanggil Kim, Ji Young Hyun, Hyun Soo Lee, Injae Shin
Summary: The epidermal growth factor receptor (EGFR) is a cell-surface glycoprotein involved in cell proliferation and tumor development. This study used a fluorescently labeled EGFR to investigate its time-dependent endocytosis in live cells and found that appended glycans affect EGFR internalization. Additionally, the study detected sialic acid residues attached to EGFR on the live cell surface using FRET-based imaging. This research provides valuable insights into the cellular functions of EGFR.
Article
Chemistry, Multidisciplinary
Subhankar Sahu, Lokesh Kumar, Sumita Das, Dipti Gupta, Ruchi Anand
Summary: This study proposes a strategy that combines organic electronics with biosensor scaffolds to create a compact device for monitoring environmental aromatic pollution. By coupling biosensing protein MopR with an organic electrochemical transistor (OECT), a sensor module capable of efficient detection of phenol was designed. Exclusive phenol detection with minimal loss of sensitivity could be achieved in complex pollutant mixtures and real environmental samples.
Review
Chemistry, Multidisciplinary
Changseok Lee, Hyung-Joon Kang, Sungwoo Hong
Summary: The formation of C-N bonds through hydroamination reactions catalyzed by nickel hydrides has been a topic of recent interest. This approach offers a way to efficiently transform a variety of alkene and alkyne substrates into compounds enriched with C-N bonds. The review provides a concise overview of the underlying reaction mechanisms and aims to stimulate further progress in NiH-catalytic techniques and catalyst design.
Article
Chemistry, Multidisciplinary
Yueci Wu, Lu-Lu Sun, Hai-Hao Han, Xiao-Peng He, Weiguo Cao, Tony D. James
Summary: Drug-induced liver injury (DILI) is a common cause of acute liver failure in the USA and Europe, but most cases can be recovered or prevented by discontinuing the offending drug. Recent research has found that peroxynitrite (ONOO-) can be used as a potential indicator for early diagnosis of DILI, and there is an urgent need to establish a method to detect and track peroxynitrite in DILI cases. In this study, a FRET-based nano fluorescent probe CD-N-I was developed, which showed high selectivity and sensitivity in detecting peroxynitrite. The probe successfully detected exogenous peroxynitrite in live cells and endogenous peroxynitrite in APAP-induced liver injury of HepG2 cells.
Article
Chemistry, Multidisciplinary
Dmitry L. Lipilin, Mikhail O. Zubkov, Mikhail D. Kosobokov, Alexander D. Dilman
Summary: This article describes a direct photocatalytic method for the thiolation of unprotected acids, which was previously challenging. By using a thionocarbonate reagent with an N-O bond, the efficient conversion of carboxylic acids to thiols is achieved.
Article
Chemistry, Multidisciplinary
Jason Malenfant, Lucille Kuster, Yohann Gagne, Kouassi Signo, Maxime Denis, Sylvain Canesi, Mathieu Frenette
Summary: Raman microscopy can reveal compound-specific vibrational fingerprints without sample preparation. The combination of efficient theoretical calculations and a user-friendly software can accurately predict peak positions and provide match scores to assist with structure determination.
Article
Chemistry, Multidisciplinary
Jayoh A. Hernandez, Paul S. Micus, Sean Alec Lois Sunga, Luca Mazzei, Stefano Ciurli, Gabriele Meloni
Summary: Essential trace metals play crucial roles in the survival and virulence of bacterial pathogens. Helicobacter pylori requires nickel for colonization and persistence in the stomach, and NixA is an essential nickel transporter in this process. This study characterizes the selectivity and electrogenic nature of NixA-mediated nickel transport.
Article
Chemistry, Multidisciplinary
Tarali Devi, Kuheli Dutta, Jennifer Deutscher, Stefan Mebs, Uwe Kuhlmann, Michael Haumann, Beatrice Cula, Holger Dau, Peter Hildebrandt, Kallol Ray
Summary: This study emphasizes the importance of subtle electronic changes and secondary interactions in the stability of biologically relevant metal-dioxygen intermediates. It also shows that the role of the chloride ligand in stabilizing the Fe-III-(OOBu)-Bu-t moiety can extend to other anions, including the thiolate ligand.
Article
Chemistry, Multidisciplinary
Jacqueline R. Santhouse, Jeremy M. G. Leung, Lillian T. Chong, W. Seth Horne
Summary: By studying the folding kinetics and mechanism of the BdpA sequence, researchers found that altering the backbone connectivity can affect protein folding. This suggests that protein mimetic chains have a significant degree of plasticity in transitioning between unfolded and folded states.
Article
Chemistry, Multidisciplinary
Divanshu Gupta, Ralf Einholz, Holger F. Bettinger
Summary: This study presents the first direct spectroscopic evidence of a cyclic seven-membered iminoborane. Compared to linear amino-iminoboranes, this cyclic iminoborane exhibits weakened bond strength and lower Lewis acidity value. The study suggests that the reduced ring strain of cyclic iminoborane prevents nitrogen fixation but allows facile (2 + 2) cycloaddition reaction with C2H4.
Article
Chemistry, Multidisciplinary
Renny Mathew, Aniruddha Mazumder, Praveen Kumar, Julie Matula, Sharmarke Mohamed, Petr Brazda, Mahesh Hariharan, Brijith Thomas
Summary: This study reveals the packing arrangement of partially disordered nitro-perylenediimide (NO2-PDI) using a synergistic approach that combines 3D ED, ssNMR, and DFT techniques. By overcoming these challenges, this methodology opens up new avenues for material characterization, driving exciting advancements in the field.
