Article
Chemistry, Physical
Yingqi Xia, Yingtang Ning, Minjie Liu, Fen -Er Chen
Summary: A poly(ethylene glycol) supported amino alcohol has been developed as a chiral ligand for the copper-catalyzed asymmetric nitrolaldol reaction. The catalyst enables the synthesis of syn-2-nitro-1,3-diols with high yields and stereoselectivities. The PEG moiety allows for easy purification and recycling of the catalyst.
JOURNAL OF CATALYSIS
(2023)
Article
Chemistry, Organic
Yuliya V. Rassukana, Alona S. Cherednichenko, Svitlana V. Shishkina, Petro P. Onys'ko
Summary: A diastereoselective addition reaction of nitromethane to the C=N bond of fluorine containing Ellman's aldimines has been successfully developed. The resulting β-nitrosulfinylamides have shown synthetic potential by conversion into optically active α-fluoroalkylated 1,3-nitroamines, 1,3-diamines, and 4-fluoroalkylated imidazolidin-2-ones.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Physical
Zinnia Arora, Diana-Ioana Eftemie, Adela Spinciu, Catalin Maxim, Ana-Maria Hanganu, Madalina Tudorache, Bogdan Cojocaru, Octavian D. Pavel, Pascal Granger, Marius Andruh, Vasile Parvulescu
Summary: Cyanosilylation, aldol coupling, and asymmetric Henry reactions were carried out using L- and D-Valmet ligands in different configurations, including immobilized copper(II) complexes onto graphene oxide (GO) which showed enhanced catalytic performance, leading to increased conversion and ee values for the reactions.
Article
Chemistry, Multidisciplinary
Stuart C. D. Kennington, Saul F. Teloxa, Miguel Mellado-Hidalgo, Oriol Galeote, Sabrina Puddu, Marina Bellido, Pedro Romea, Felix Urpi, Gabriel Aullon, Merce Font-Bardia
Summary: A direct and asymmetric aldol reaction of N-acyl thiazinanethiones with aromatic aldehydes catalyzed by chiral nickel(II) complexes was reported. The reaction gives high yields of O-TIPS-protected anti-aldol adducts with remarkable stereocontrol and atom economy. The removal of the achiral scaffold provides enantiomerically pure intermediates with synthetic interest for producing anti-alpha-amino-beta-hydroxy and alpha,beta-dihydroxy carboxylic derivatives, with theoretical calculations explaining the observed high stereocontrol.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Yu-Heng Wang, Xi-Rui Wang, Ke-Lan Xu, Zi-Yue Chen, Bo-Wen Pan, Li-Jun Peng, Ying Zhou, Xiong-Li Liu
Summary: This paper describes the first example of umpolung & alpha;-regioselective 1,3-dipolar cycloaddition of optically pure perhydroindole-2-carboxylic acid 1a with pyridinecarboxaldehydes 2. Using this practical method, a wide range of conformationally rigid chiral perhydroindole-bipyridine compounds 3 can be easily prepared with good results, and their diastereoisomers can also be isolated by column chromatography. Furthermore, the diverse derivatization of products 3 into 1,2-oxazinane-containing diverse bipyridine compounds 6 has been successfully demonstrated using m-CPBA as the oxidant.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Yu-Heng Wang, Xi-Rui Wang, Ke-Lan Xu, Zi-Yue Chen, Bo-Wen Pan, Li-Jun Peng, Ying Zhou, Xiong-Li Liu
Summary: Here, we describe the first example of umpolung alpha-regioselective 1,3-dipolar cycloaddition between optically pure perhydroindole-2-carboxylic acid 1a and pyridinecarboxaldehydes 2. Using this practical method, a variety of conformationally rigid chiral perhydroindole-bipyridine compounds 3 can be efficiently prepared, and their diastereoisomers can be separated by column chromatography. Additionally, we demonstrate the diverse derivatization of products 3 into 1,2-oxazinane-containing bipyridine compounds 6, facilitated by the oxidant m-CPBA. The high efficiency of these chemical transformations is attributed to the in situ-generated byproduct 3-chlorobenzoic acid, which acts as an internal reuse reagent for subsequent ring-opening and ring-expansion reactions mediated by formal oxygen atom insertion into the carbon-nitrogen bond.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Review
Chemistry, Physical
Beiqi Yang, Aiwen Yu, Yuanhua Wang
Summary: 1,3-Diamines are important in the synthesis of biologically active molecules, but there have been fewer studies compared to 1,2-diamines. Non-catalytic methods in this direction have not been well-explored. The direct construction of C-N bonds by metal- or non-metal-catalyzed C-H functionalization is an efficient approach, especially for non-specialized substrates. Here, we summarize innovative methods for the synthesis of 1,3-diamines in the past five years, including non-catalytic reactions and metal- or non-metal-catalyzed reactions.
Article
Chemistry, Physical
Kosuke Higashida, Valentin Smail, Haruki Nagae, Jean-Francois Carpentier, Kazushi Mashima
Summary: We achieved a nickel(0)-catalyzed asymmetric allylic alkylation reaction of beta-dicarbonyl compounds under ambient conditions, resulting in high yields of quaternary chiral compounds with high enantioselectivity.
Article
Chemistry, Inorganic & Nuclear
Juhyun Cho, Saira Nayab, Jungkyu K. Lee, Jong Hwa Jeong, Hyosun Lee
Summary: In this study, two diastereopure camphor-derived iminomethylpyridine ligands were used to synthesize copper(II) complexes. These complexes were characterized by single-crystal X-ray diffraction and found to be efficient catalysts for the enantioselective Henry reaction. The ligand backbone and side-chain contributed to the excellent enantioselectivities observed.
INORGANIC CHEMISTRY COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Jiao Long, Yuqiang Li, Weining Zhao, Guoyin Yin
Summary: The study introduces a novel asymmetric nickel/Bronsted acid dual-catalyzed reaction for the synthesis of chiral allylic phosphine oxides, featuring economic efficiency, broad substrate scope, and high selectivity. Preliminary mechanistic investigations suggest a highly regioselective process for 1,3-diene insertion into chiral Ni-H species and an irreversible step for chiral C-P bond formation.
Article
Chemistry, Multidisciplinary
Kengo Hanaya, Kaho Yamoto, Kazuaki Taguchi, Kazuaki Matsumoto, Shuhei Higashibayashi, Takeshi Sugai
Summary: The chemical modification of proteins is an effective technique for manipulating protein properties and functions. This paper proposes a simple method using a copper(II)-mediated aldol reaction to selectively modify the N-terminus of peptides and proteins.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Runping Wang, Jingfan Luo, Chunmei Zheng, Hongyun Zhang, Lu Gao, Zhenlei Song
Summary: An O-2-assisted, four-component reaction has been developed for the synthesis of a wide range of syn-1,3-amino alcohols in one step. The approach allows diastereoselective synthesis of anti/syn- and syn/syn-3-amino-1,5-diols with high yields and diastereoselectivity. The method was demonstrated in the efficient four-step synthesis of the piperidine alkaloid (-)-2'-epi-ethylnorlobelol.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Saul F. Teloxa, Miguel Mellado-Hidalgo, Stuart C. D. Kennington, Pedro Romea, Felix Urpi, Gabriel Aullon, Merce Font-Bardia
Summary: A direct and asymmetric aldol reaction between N-azidoacetyl-1,3-thiazolidine-2-thione and aromatic aldehydes catalyzed by a chiral nickel(II)-Tol-BINAP complex has been developed. The reaction gives anti alpha-azido-beta-silyloxy adducts with excellent stereocontrol and high yields. The removal of thiazolidinethione allows for the synthesis of a wide array of enantiomerically pure derivatives, providing a new route to di- and tripeptide blocks containing a beta-aryl-beta-hydroxy-alpha-amino acid.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Multidisciplinary
Adrian Moreno Gonzalez, Kieran Nicholson, Natalia Llopis, Gary S. Nichol, Thomas Langer, Alejandro Baeza, Stephen P. Thomas
Summary: In this study, high oxidation-state carbonyl coupling partners were reacted with enones using two-fold organoborane catalysis to directly obtain aldol-type products. This new retrosynthetic disconnection method is compatible with enolisable coupling partners and achieves excellent chemoselectivity and substrate scope.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Daniel Luecke, Markus Kalesse
Summary: Our work presents a Kiyooka aldol protocol for the stereoselective synthesis of tertiary alcohols. This methodology is suitable for simple aromatic or aliphatic aldehydes, as well as more complex substrates with a chiral center. We observed an unexpected dependency between stereoselectivity and double-bond geometry of the ketene acetal, and also demonstrated applications in the synthesis of natural products.
Article
Chemistry, Organic
Madhu Babu Tatina, Xia Mengxin, Rao Peilin, Zaher M. A. Judeh
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Pharmacology & Pharmacy
Shuddhodana, Zaher Judeh
JOURNAL OF DRUG DELIVERY SCIENCE AND TECHNOLOGY
(2019)
Article
Materials Science, Biomaterials
Shuddhodana, Pooi Wen Kathy Wong, Zaher Judeh
MATERIALS SCIENCE AND ENGINEERING C-MATERIALS FOR BIOLOGICAL APPLICATIONS
(2020)
Review
Chemistry, Multidisciplinary
Ziad Moussa, Zaher M. A. Judeh, Marwa A. M. Sh El-Sharief, Ahmed M. Sh El-Sharief
Article
Chemistry, Physical
Pappu Lakshmi Madhuri, Shuddhodana, Zaher M. A. Judeh, Ibrahim Abdulhalim
PARTICLE & PARTICLE SYSTEMS CHARACTERIZATION
(2020)
Article
Chemistry, Organic
Madhu Babu Tatina, Wang Xinzhu, Mardi Santoso, Ziad Moussa, Zaher M. A. Judeh
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Mengxin Xia, Mallikharjuna Rao Lambu, Madhu Babu Tatina, Zaher M. A. Judeh
Summary: This study developed a practical and efficient three-component reaction to synthesize densely functionalized pyrroles from common carbohydrates. The cascade reaction showed high selectivity and catalytic efficiency, suitable for large-scale synthesis and further transformation to more complex structures. The work represents a significant advancement in sustainable synthesis of these ubiquitous heterocycles.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Surabhi Devaraj, Yew Mun Yip, Parthasarathi Panda, Li Lin Ong, Pooi Wen Kathy Wong, Dawei Zhang, Yusuf Ali, Zaher Judeh
Summary: This study reveals the potential of Feruloyl Sucrose Esters (FSEs) as selective Alpha Glucosidase Inhibitors (AGIs) for the treatment of diabetes, with a hypothetical reduction of side effects associated with commercial AGIs.
CURRENT MEDICINAL CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Ziad Moussa, Zaher M. A. Judeh, Ahmed Alzamly, Saleh A. Ahmed, Harbi Tomah Al-Masri, Bassam Al-Hindawi, Faisal Rasool, Sara Saada
Summary: This study demonstrates the effectiveness of the I-2-DMSO oxidative system in the synthesis of N-arylcyanoformamides. The method offers mild conditions, broad substrate scope, and high reaction efficiency. Furthermore, it provides a great approach for the synthesis of 2-cyanobenzothiazoles.
Article
Multidisciplinary Sciences
Mardi Santoso, Li Lin Ong, Nur Pasca Aijijiyah, First Ambar Wati, Azminah Azminah, Rose Malina Annuur, Arif Fadlan, Zaher M. A. Judeh
Summary: The synthesized 3,3-di(indolyl)indolin-2-ones exhibited higher α-glucosidase inhibitory activities and lower α-amylase inhibitory activities. Compound 1i showed the most favorable inhibitory activity. Docking studies further supported the observed inhibitory activities. These results suggest that 3,3-di(indolyl)indolin-2-ones may serve as suitable α-glucosidase inhibitors, and the lower α-amylase activity could reduce side effects.
Article
Chemistry, Organic
Xia Mengxin, Mallikharjuna Rao Lambu, Zaher M. A. Judeh
Summary: This study develops a simple reaction method to embed nitrogen into sugars to produce valuable N-heterocyclic compounds. The method has a wide substrate scope, and achieves high selectivity by controlling the sequence of substrate addition.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Mengxin Xia, Ziad Moussa, Zaher M. A. Judeh
Summary: A simple and efficient method for the direct conversion of unprotected carbohydrates to N-heterocycles has been developed. This method features mild reaction conditions, broad substrate scope, and excellent scalability.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Li Lin Ong, Pooi Wen Kathy Wong, Surhabi Deva Raj, Duc Thinh Khong, Parthasarathi Panda, Mardi Santoso, Zaher M. A. Judeh
Summary: Phenylpropanoid sucrose esters (PSEs), important plant-derived metabolites, are challenging to synthesize accurately. This study presents a synthesis strategy for PSEs via orthogonal protection/deprotection and selective cinnamoylation, demonstrating the synthesis of several cinnamoylated PSEs.
NEW JOURNAL OF CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
First Ambar Wati, Mardi Santoso, Ziad Moussa, Sri Fatmawati, Arif Fadlan, Zaher M. A. Judeh
Summary: Trisindolines are heterocyclic nitrogen compounds with diverse bioactivities, synthesized by reacting isatins with indoles, showing anticancer, antimicrobial, antitubercular, antifungal activities, among others.
Article
Chemistry, Multidisciplinary
Madhu Babu Tatina, Ziad Moussa, Mengxin Xia, Zaher M. A. Judeh
CHEMICAL COMMUNICATIONS
(2019)
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.
