Article
Chemistry, Multidisciplinary
Zhaobin Wang, Ze-Peng Yang, Gregory C. Fu
Summary: The development of efficient methods, particularly catalytic and enantioselective processes, for the construction of all-carbon quaternary stereocentres is an important and difficult challenge in organic synthesis. A nickel-based chiral catalyst has been shown to achieve enantioconvergent couplings of tertiary electrophiles with alkenylmetal nucleophiles, providing access to a variety of organic compounds with good yield and enantioselectivity. This approach offers a potentially versatile strategy for the synthesis of complex molecules, including natural product intermediates.
Article
Chemistry, Multidisciplinary
Cheng Sheng, Zheng Ling, Junzhe Xiao, Kai Yang, Xie Fang, Shengming Ma, Wanbin Zhang
Summary: In this study, enantio- and diastereoselective α-additions of 1-alkynyl ketimines with dual-copper-catalysis were successfully achieved under mild conditions, leading to the synthesis of chiral tetrasubstituted α-amino allenoates bearing a vicinal all-carbon quaternary stereocenter in high yields (up to 99% yield) with excellent enantioselectivities (up to 99% ee) and diastereoselectivities (up to >20:1 dr). The stereodivergent synthesis of the products was realized by the asymmetric α-addition reaction and the Grignard reagent promoted epimerization. Importantly, the reaction could be smoothly scaled up and applied to introduce chiral tetrasubstituted allenyl moieties into bioactive molecules.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Chiara Portolani, Giovanni Centonze, Sara Luciani, Andrea Pellegrini, Paolo Righi, Andrea Mazzanti, Alessia Ciogli, Andrea Sorato, Giorgio Bencivenni
Summary: The first catalytic enantioselective and diastereoselective synthesis of atropisomeric hydrazides was achieved using a sequential catalysis protocol, providing a stereodivergent approach to enantioenriched atropisomeric hydrazides. The resulting axially chiral hydrazides were obtained directly from commercially available reagents in high yields and with good stereocontrol, demonstrating the effectiveness of this strategy.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
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
Xiaosa Lu, Jie Zhu, Yinhua Huang
Summary: A rhodium-catalyzed highly enantio- and diaster-eoselective alkenylation reaction of Ay-unsaturated butenolides is reported. The use of a chiral diene ligand enables the synthesis of chiral butyrolactones in high yields with extremely high enantioselectivities and high diastereoselectivities. The key process involves the isomerization of butenolides and subsequent dynamic kinetic resolution.
Article
Chemistry, Organic
Fang Xie, Jie Zhao, Deyue Ren, Jianming Xue, Jingyi Wang, Qin Zhao, Lu Liu, Xiaodan Liu
Summary: A Cu-catalyzed coupling reaction between cyclic imino esters and 2H-azirines has been developed, allowing for the synthesis of novel optically active aziridines in high yields and with excellent levels of diastereo- and enantioselectivities under mild conditions. This method features a broad substrate scope, good functional group compatibility, and enriches the existing reaction type for the rapid synthesis of optically active aziridines bearing vicinal tetrasubstituted stereogenic carbon centers.
Article
Chemistry, Organic
Gujjula V. Ramakrishna, Rodney A. Fernandes
Summary: In this study, an efficient diastereoselective allylation of aldehydes with functionalized allyl bromolactone was utilized to achieve the protecting-group-free divergent total synthesis of various guaianolides (+)-ligustrin, (+)-8-epi-ligustrin, and (+)-grosheimin, as well as the formal synthesis of (-)-eupalinilide E.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Organic
D. H. Sreenivasa Rao, Ayon Chatterjee, Santosh Kumar Padhi
Summary: Chiral beta-nitroalcohols are important building blocks in organic synthesis, and biocatalytic methods have gained significant importance for their asymmetric synthesis. Different biocatalytic strategies, such as kinetic resolution and Henry reaction, have been developed for the asymmetric synthesis of beta-nitroalcohol stereoisomers.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Hyun Ji Jeon, Su Min Park, Yu Lim Lee, Sang-gi Lee
Summary: The palladium-catalyzed divergent asymmetric synthesis of chiral spiro-furanindoline derivatives is described. The zwitterionic alkoxy pi-allyl Pd(II) intermediate, generated catalytically from vinyl ethylene carbonate (VEC), could undergo ligand-controlled enantio-and diastereoselective dipolar [3 + 2] spiroannulation with indole-based azadienes to afford the optically active spiro-furanindolines embedding an all-carbon quaternary stereocenter in high yields (up to 99%) with good to excellent stereoselectivities (up to 99% ee and up to >94:6 dr).
Article
Chemistry, Organic
Laxman Devidas Khalse, Sachin S. Gorad, Prasanta Ghorai
Summary: In this study, a new Cu(II)-(S,S)-Pr-i-FOXAP catalyst was reported for the borylative Michael/Michael addition cascade cyclization of unsymmetrical dienone, leading to the synthesis of highly substituted and functionalized spiroindane boronates under mild conditions. A series of optically active spiroids bearing boronic ester were obtained with excellent yields and good to excellent enantioselectivities and diastereoselectivities.
Article
Chemistry, Multidisciplinary
Daniel Moock, Tobias Wagener, Tianjiao Hu, Timothy Gallagher, Frank Glorius
Summary: This study presents a method for enantio- and diastereoselective hydrogenation of multiply substituted benzofurans in a one-pot cascade catalysis, allowing controlled installation of up to six new defined stereocenters to produce complex octahydrobenzofurans prevalent in bioactive molecules. The unique combination of a chiral homogeneous ruthenium-N-heterocyclic carbene complex and an in situ activated rhodium catalyst from a complex precursor enables the process.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Tianhong Wang, Youbin Peng, Guanlin Li, Yicong Luo, Yong Ye, Xiaohong Huo, Wanbin Zhang
Summary: The highly regio-, enantio-, and diastereoselective allylic alkylation of 3-alkyl oxindoles through synergistic iridium and copper catalysis provides a series of 3,3-disubstituted oxindole derivatives containing adjacent quaternary and tertiary stereogenic centers in excellent yields, enantiomeric excess, and diastereomeric ratio. The method demonstrates exclusive branched selectivity, excellent enantio- and diastereoselectivities, and good functional compatibility, with the chiral copper catalyst being crucial for achieving high reactivities and diastereoselectivities under mild reaction conditions.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Yan-Li Xu, Zhou-Zhou Qin, Yu-Xia Wang, Peng-Fei Zhao, Hong-Feng Li, Zhi-Hong Du, Chao-Shan Da
Summary: Highly enantiopure and bioactive delta-valerolactones and pyrazolones, bearing alpha-all-carbon quaternary stereocentres, were successfully synthesized via a one-pot procedure using a new chiral squaramide catalyst. This method is economically efficient and environmentally benign, starting from readily available, inexpensive materials.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Michael Schrempp, Raphael Wagner, Hermann Gleich, Andreas Gansaeuer, Dirk Menche
Summary: A versatile titanocene-catalyzed radical allyl transfer reaction on epoxides has been reported, which enables efficient coupling of variously substituted allyl sulfones and the formation of quaternary carbon centers, providing a convenient method for further organic synthesis.
Article
Chemistry, Multidisciplinary
Shibaram Panda, Upasana Gayen, Prasanta Ghorai
Summary: This study describes the first organocatalytic, non-destructive desymmetrisation of 3-substituted cyclobutanone followed by intramolecular cyclisation. The use of cinchona-derived squaramide catalyst effectively enables the intramolecular Michael addition of cyclobutanone to enones, resulting in the formation of [6,5,4]-fused carbocyclic skeleton with good yields and excellent diastereo- and enantioselectivities. Moreover, this method provides an alternative pathway for the synthesis of enantioenriched high-value products like gamma-lactones and indan-2-ol derivatives.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Agriculture, Multidisciplinary
David Mangan, Barry V. McCleary, Helena Culleton, Claudio Cornaggia, Ruth Ivory, Vincent A. McKie, Elaine Delaney, Tadas Kargelis
JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE
(2019)
Article
Chemistry, Multidisciplinary
Aaron Gutierrez Collar, Cristina Trujillo, Bruce Lockett-Walters, Brendan Twamley, Stephen J. Connon
CHEMISTRY-A EUROPEAN JOURNAL
(2019)
Article
Chemistry, Multidisciplinary
Aaron Gutierrez Collar, Cristina Trujillo, Stephen J. Connon
CHEMISTRY-A EUROPEAN JOURNAL
(2019)
Article
Chemistry, Multidisciplinary
Simon N. Smith, Ryan Craig, Stephen J. Connon
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Article
Chemistry, Multidisciplinary
Simon P. Curran, Brendan J. Fallon, Stephen J. Connon
Article
Biochemistry & Molecular Biology
Claire Fergus, Mashael Al-Qasem, Michelle Cotter, Ciara M. McDonnell, Emiliano Sorrentino, Franciane Chevot, Karsten Hokamp, Mathias O. Senge, John M. Southern, Stephen J. Connon, Vincent P. Kelly
Summary: Base modification can occur throughout a transfer RNA molecule, with a particular emphasis on position 34 of the anticodon loop. Human enzymes can recognize a wide range of artificial derivatives for transfer RNA incorporation, while displaying strict specificity for decoding certain codons. Exploiting the queuosine incorporation pathway shows broad potential for intentionally engineering chemical diversity into transfer RNA anticodons.
NUCLEIC ACIDS RESEARCH
(2021)
Article
Chemistry, Organic
Mili Litvajova, Emiliano Sorrentino, Brendan Twamley, Stephen J. Connon
Summary: This study demonstrates the application of N-protected oxindole derivatives with unprecedented malleability in enantioselective phase-transfer-catalysed alkylations. By optimizing the structure of the catalyst, high levels of enantioselectivity were achieved. It was found that urea-based catalysts outperformed squaramide derivatives, and that installing a chlorine atom in the quinoline moiety of the catalyst improved reaction selectivity.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Simon N. Smith, Stephen J. Connon
Summary: The ring contraction-lactamisation of anhydrides with trimethylsilylazide in the presence of an amine catalyst has been studied. It is possible to generate 5,- 6- and 8-membered ring lactams from cyclic anhydrides under controlled conditions, with a simple operation procedure. Succinic anhydrides can be used to produce N-carboxyanhydrides for polymer chemistry and as beta-peptide precursors.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Cristina Trujillo, Sarah A. Cronin, Stephen J. Connon
Summary: A complete computational study was conducted to rationalize a new organocatalytic approach for the kinetic resolution of 4-substituted oxazinones, resulting in highly enantioenriched beta-amino acids. The study also investigated the alcoholytic kinetic resolution of a 7-memebered ring analogue for the first time, generating enantioenriched gamma-amino acids.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Medicinal
Ciara M. McDonnell, Magda Ghanim, J. Mike Southern, Vincent P. Kelly, Stephen J. Connon
Summary: This study investigates the impact of modified beta-lysines on the growth rates of eubacterial cells. The results indicate that the observed effects are due to the post translational modification of Elongation Factor P (EFP) catalyzed by PoxA. The promiscuity of PoxA allows for examination of a wide range of exogenous beta-lysines.
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
(2022)
Article
Chemistry, Organic
Sarah A. Cronin, Stephen J. Connon
Summary: This study introduces a novel approach to catalytic, alcoholytic kinetic resolution of oxazinones using a stereochemically dense cinchona alkaloid-based catalyst. The catalyst enables highly enantiodiscriminatory ring-opening of oxazinones equipped with electrophilic aryl units, leading to the generation of orthogonally protected beta-amino acids for the first time.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Eoghan G. Delany, Stephen J. Connon
Summary: The enantioselective intermolecular crossed-benzoin condensation mediated by novel chiral N-heterocyclic carbenes derived from pyroglutamic acid has been investigated. Increasing both the steric requirement and the electron-withdrawing characteristics of the N-aryl ring led to more chemoselective, efficient and enantioselective chemistry. Subsequent protocol optimization involving o-substituted benzaldehyde as one reacting partner allowed a range of crossed-benzoins to be synthesized in moderate-good yields with moderate to excellent enantioselectivity.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Mashael A. Alqasem, Claire Fergus, J. Mike Southern, Stephen J. Connon, Vincent P. Kelly
CHEMICAL COMMUNICATIONS
(2020)
Article
Chemistry, Multidisciplinary
Amy C. Maguire, Vikas Kumar, Stephen J. Connon
CHEMICAL COMMUNICATIONS
(2019)
Article
Chemistry, Multidisciplinary
Bruce Lockett-Walters, Cristina Trujillo, Brendan Twamley, Stephen Connon
CHEMICAL COMMUNICATIONS
(2019)
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)
