Review
Biochemistry & Molecular Biology
Gheorghe Ilia, Vasile Simulescu, Nicoleta Plesu, Vlad Chiriac, Petru Merghes
Summary: Carbonyl olefinations are important organic syntheses for forming C=C bonds, often with high yields and excellent stereoselectivity. The Wittig reaction is a well-known carbonyl olefination method, involving the reaction between an aldehyde or ketone and a Wittig reagent. The use of ultrasound in these reactions, including modified Wittig syntheses, has been studied for green synthesis and improved yields and reaction times.
Article
Chemistry, Organic
Paul C. Ruer, Youssef Nassar, Peter Polak, Janine Cossy
Summary: Five-membered exo-glycals were synthesized from six-membered 2-iodo-endo-glycals through a metal/halogen exchange/ring-opening sequence followed by a cyclization catalyzed by Ag2CO3.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Simona Fazekasova, Jozef Gonda, Miroslava Martinkova, Martina Bago Pilatova, Monika Majirska, Veronika Turcanova, David Jager
Summary: A short synthetic route towards novel cytotoxic FTY720 analogues with variously substituted azo-benzene units was developed. The target compounds were constructed using Wittig olefination or Mills reaction as key processes. Preliminary biological screening showed promising antiproliferative activity of the newly synthesised derivatives against Jurkat, HeLa, and HCT-116 cells, comparable or higher than cisplatin. The structure-activity relationship indicated that the loss of the alkyl side chain or its substitution with a hydroxymethyl group on the azobenzene core seemed to be detrimental for the resulting cytotoxic profile. To probe the photochromic properties, the reversible E/Z isomerization and thermal relaxation rate of the final derivatives were determined.
Article
Chemistry, Physical
Bing-ru Shao, Wen-feng Jiang, Chao Zheng, Lei Shi
Summary: The precise synthesis of axially chiral molecules is highly valuable in pharmaceutics, fine chemicals, and materials science. However, the enantioselective synthesis of non-atropisomeric axially chiral alkylidene cycloalkanes has been a great challenge due to the remote distance between chirality-related groups or atoms. We developed a general efficient methodology using palladium-catalyzed asymmetric allylic alkylation, which showed excellent enantioselectivities, high yields, and a wide substrate scope. The additive effect played a crucial role in improving the chem- and enantioselectivity of this reaction. Due to the value and structural diversity of the products, this method provides an opportunity for further exploration of the applied potential of axially chiral olefins in related research fields.
Editorial Material
Chemistry, Multidisciplinary
Moumita Majumdar
Summary: Monomeric stibine oxide has been difficult to obtain due to the large antimony orbitals and the high electronegativity difference with oxygen. However, a free tris(2,6-diisopropylphenyl)stibine oxide has been isolated and can serve as an oxo-transfer reagent.
Article
Biochemistry & Molecular Biology
Ignacy Janicki, Piotr Kielbasinski
Summary: This report presents new, easily accessible reagents for highly Z-selective HWE reactions, demonstrating very good Z-selectivity and high yields in most cases. The application of these new reagents may provide a valuable and practical alternative to the well-established Still-Gennari or Ando Z-selective carbonyl group olefination protocols.
Article
Chemistry, Applied
Seung Jong Lee, Hyung Wook Moon, Kee-Young Lee, Chang Young Oh, U. Bin Kim, Hyunik Shin
Summary: A highly convergent, gram-scale synthesis of vitamin D3 analogue tacalcitol 1 is achieved through optimized reaction steps and a synthetic route, starting from simple starting materials. This method allows for efficient and scalable synthesis of a complex vitamin D3 analogue.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2021)
Article
Chemistry, Organic
Alexandra E. Golliher, Antonio J. Tenorio, Brandon M. Cornali, Erika Y. Monroy, Rodolfo Tello-Aburto, F. Omar Holguin, William A. Maio
Summary: Enamides are a unique structural moiety found in natural products and synthetic derivatives. This report discloses a novel, metal-free method for the synthesis of trans-gamma-chloro-enamides from the union of acrolein with secondary amides, followed by S(N)2 displacement reactions to access various trans-gamma-functionalized-enamides. Further reactions of two derivatives led to the formation of novel triazole products and di-and trienamide-containing materials.
Article
Chemistry, Organic
Ignacy Janicki, Piotr Kielbasinski
Summary: The Z-selective Still-Gennari and Ando modifications of the Horner-Wadsworth-Emmons reaction are valuable synthetic tools in organic chemistry. A purification-free procedure for the synthesis of these reagents has been presented, resulting in high purity products on a gram scale. Additionally, a novel Still-Gennari type reagent has been synthesized, which may exhibit improved Z-selectivity in olefinations.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Organic
Dario Filippini, Mattia Silvi
Summary: This article introduces a functional group tolerant and transition-metal-free conjunctive olefination reaction and analyzes its conceptual background and key aspects of development.
Article
Chemistry, Organic
Weiwei Jin, Shouyun Yu
Summary: The photoinduced and palladium-catalyzed remote desaturation of O-acyl hydroxamides to unsaturated amides under mild conditions has been achieved efficiently and selectively. This method features good site-selectivity, is terminal oxidant-free, and produces moderate to excellent yields for a variety of unsaturated amides, enabling late-stage desaturation of complex and biologically important molecules.
Article
Biotechnology & Applied Microbiology
Zhangde Long, Kena Li, Yun Xue, Yongwei Sun, Jigang Li, Zan Su, Jiansheng Sun, Qibin Liu, Hong Liu, Tao Wei
Summary: A novel ene-reductase (KaDBR1) was purified and characterized from Kazachstania exigua HSC6 for the synthesis of dihydro-beta-ionone from beta-ionone. The purified enzyme had optimal activity at 60 degrees C and pH 6.0, and it favored NADH over NADPH as a cofactor. The catalytic efficiency of KaDBR1 using NADH was 8.1-fold greater than when using NADPH. Owing to its unique properties, KaDBR1 is a potential candidate for the enzymatic biotransformation of beta-ionone to dihydro-beta-ionone in biotechnology applications.
BIOTECHNOLOGY LETTERS
(2023)
Article
Chemistry, Organic
Joseph Tadros, Christian Dankers, Janice R. Aldrich-Wright, Anastasios Polyzos, Christopher P. Gordon
Summary: The development of a continuous flow, solid-phase triphenylphosphine (PS-PPh3) assisted protocol for in situ coupling of halogen and carbonyl functionalised molecular pairs by Wittig olefination within 15 mins is described. This method uses a traditional polystyrene-based immobilisation matrix and expands the substrate scope to substituted ketones, secondary alkyl chlorides, and an unprotected maleimide scaffold.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Eedubilli Srinivas, Vavilapalli Satyanarayana, Jhillu Singh Yadav
Summary: Two different strategies were considered for the total synthesis of metacridamides A and B. The first approach based on Horner-Wittig olefination reaction was unsuccessful. The second approach, involving several reactions, successfully synthesized an advanced intermediate 39 with all stereocenters present in metacridamides A and B.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Organic
Shu Li, Jian-Lin Xu, Yun-He Xu
Summary: A novel strategy of copper-catalyzed regio- and enantioselective hydrosilylation of 4-substituted vinylidenecyclo-hexanes with silanes was developed, which afforded the corresponding (cyclohexylidene)ethyl silanes in moderate to high yields with good enantioselectivities.
Article
Engineering, Electrical & Electronic
Te Hu, Yuchang Su, Ian R. Baxendale, Yaping Zhang, Jinfan Zhu
JOURNAL OF ELECTRONIC MATERIALS
(2020)
Article
Chemistry, Organic
Michele Ruggeri, Amanda W. Dombrowski, Stevan W. Djuric, Ian R. Baxendale
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Biochemistry & Molecular Biology
Guido Gambacorta, David C. Apperley, Ian R. Baxendale
Article
Chemistry, Multidisciplinary
Christoph Suster, Ian R. Baxendale, Marko D. Mihovilovic, Christian Stanetty
FRONTIERS IN CHEMISTRY
(2020)
Article
Chemistry, Organic
Oliver M. Griffiths, Michele Ruggeri, Ian R. Baxendale
Review
Chemistry, Organic
Guido Gambacorta, James S. Sharley, Ian R. Baxendale
Summary: Fragrance ingredients/intermediates exhibit favorable properties for continuous-flow manufacturing and hold potential applications in the field of organic synthesis. This review showcases the advantages of utilizing a flow approach for important transformations in the fragrance and flavors industry, serving as a comprehensive compilation of techniques and apparatus from existing chemical and engineering literature.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Guido Gambacorta, Ian R. Baxendale
Summary: In this study, a continuous-flow preparation of 2-benzoxazolinone via the Hofmann rearrangement of salicylamide using trichloroisocyanuric acid as the chlorinating agent was implemented. The system was optimized to avoid solid accumulation and enable the production of large quantities of pure desired material. Additionally, a TCCA-based chlorination of 2-benzoxazolone to the corresponding 5-chloro derivative was carried out under batch conditions.
ORGANIC PROCESS RESEARCH & DEVELOPMENT
(2022)
Article
Biochemical Research Methods
Tunca Dogan, Ece Akhan Guzelcan, Marcus Baumann, Altay Koyas, Heval Atas, Ian Baxendale, Maria Martin, Rengul Cetin-Atalay
Summary: DRUIDom is a new method that identifies bio-interactions between drug candidate compounds and targets by utilizing the domain modularity of proteins, thereby overcoming problems associated with current approaches.
PLOS COMPUTATIONAL BIOLOGY
(2021)
Article
Chemistry, Organic
Ben M. J. Lancaster, Alexander J. Nicholls, Ian R. Baxendale
Summary: This communication describes an unprecedented substitution cascade, in which 4-methylpyridine acts as a carbon nucleophile in an unusual SNAr process to form a novel triarylmethane structure. The proposed mechanism is supported by single crystal X-ray analysis, highlighting the efficient synthesis of complex triarylmethane architectures with both substituted phenyl and pyridyl aromatics in a single step.
Article
Chemistry, Organic
Alexander J. Nicholls, Ian R. Baxendale
Summary: This short note describes the synthesis of an amorphous benzo[1,2,3]dithiazole chloride salt, commonly known as Herz salt, using the Herz reaction. The conversions of this species to various useful adducts in medicinal and materials chemistry have been well established, but isolation examples in the literature and characterization data are limited. For the first time, this study provides mass spectrometry data for this compound and proposes a new mechanism of its formation based on new experimental observations and data.
Article
Materials Science, Multidisciplinary
Te Hu, Ian R. Baxendale, Yuchang Su, Fangjiang Li, Shaomi Duan, Yaping Zhang, Honxin Fan
Summary: Combining XRD pattern analysis with DSC curves and thermodynamic equations can optimize the preparation conditions of nanomaterials and improve the speed of the preparation scheme.
APPLIED PHYSICS A-MATERIALS SCIENCE & PROCESSING
(2022)
Article
Chemistry, Multidisciplinary
Gemma L. Parker, Ruben Van Lommel, Nil Roig, Mercedes Alonso, Adrian B. Chaplin
Summary: A spectroscopic and computational examination of a series of rhodium(I) pybox carbonyl complexes reveals a correlation between the conformation of the aryl-substituted oxazoline donors and the carbonyl stretching frequency. This correlation is observed in both octahedral rhodium(III) and ruthenium(II) variants and cannot be explained by the classical interpretation of metal-carbonyl bonding. Instead, it is explained by local changes in the electric field projected along the metal-carbonyl vector.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Chemistry, Organic
James S. Sharley, Guido Gambacorta, Ana Maria Collado Perez, Estela Espinos Ferri, Amadeo Fernandez Miranda, Jorge Sanchez Quesada, Ian R. Baxendale
Summary: In this study, a process for the synthesis of cyclic allylic nitro compounds using greener solvent and lower cost, more robust catalyst was developed. The optimized conditions were able to selectively synthesize important fragrance intermediates such as alpha-dehydroherbac, demonstrating their scope and utility.
Article
Chemistry, Organic
James S. Sharley, Guido Gambacorta, Ana Maria Collado Perez, Estela Espinos Ferri, Amadeo Fernandez Miranda, Isabelle Fernandez Fernandez, Jorge Sanchez Quesada, Ian R. Baxendale
Summary: A new method for the oxidation of Hedione 1 to dehydrohedione 2 has been developed based on a one-pot alpha-chlorination-elimination sequence, which allows for easy scalability. The unprecedented spontaneous elimination of alpha-chloro in methanol enables the oxidation to be carried out as a one-pot protocol, eliminating the need for multiple steps/reactions. A continuous flow process utilizing sulfuryl chloride has also been demonstrated, providing a steady and safe evolution of SO2 gas during the reaction.
Article
Multidisciplinary Sciences
James S. Sharley, Guido Gambacorta, Ana Maria Collado Perez, Estela Espinos Ferri, Amadeo Fernandez Miranda, Jorge Sanchez Quesada, Ian R. Baxendale
Summary: This article presents a dataset of spectroscopic analysis performed on starting materials, intermediates, and products related to the synthesis of Hedione. The data was collected at Durham university between October 2020 and September 2021 for the development of a preparative method to Dehydrohedione. The proton, Carbon-13, and Fluorine-19 Nuclear magnetic resonance spectra of the compounds were recorded using Varian 600 MHz and Bruker Avance-40 0 instruments. The IR spectra were recorded using a Perkin Elmer Spectrum Two UATR Two FT-IR instrument, and accurate mass measurement was performed using a Waters QtoF premier mass spectrometer.
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.
