Article
Chemistry, Organic
Joseph N. Capilato, Maxime A. Siegler, Rozhin Rowshanpour, Travis Dudding, Thomas Lectka
Summary: The behavior and reactivity of a series of steroidal alpha,beta-unsaturated hydrazones are controlled by various weak C-H hydrogen bonds, showing a unique bifurcated intramolecular C-H interaction. These steroid derivatives can undergo highly regio- and stereoselective fluorination directed by sulfonyl oxygen atoms through C-H hydrogen bonds.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Medicinal
Ana L. Perez-Castorena, Antonio Nieto-Camacho, Mahinda Martinez, Emma Maldonado
Summary: The structures of compounds from the stems and leaves as well as calyxes of Physalis grisea were determined, and the anti-hyperglycemic activity of these compounds was evaluated.
Article
Chemistry, Organic
Huili Li, Jianmin Fu, Jundong Fu, Xueji Li, Donglei Wei, Hou Chen, Liangjiu Bai, Lixia Yang, Huawei Yang, Wenxiang Wang
Summary: A visible-light metal-free photocatalytic regioselective and enantioselective alkene halofunctionalization reaction under mild conditions is described. Various terminal and internal alkenes could be transformed to α-halogenated and α,β-dibrominated derivatives with good to excellent yields in as short as 5 min reaction time. Water serves as the green nucleophile and solvent in halohydroxylation and halo oxidation reactions. Different types of products can be obtained by adjusting the reaction conditions. Moreover, sunlight demonstrates the ability to produce similar yields, showcasing a practical example of solar synthesis and offering an opportunity for solar energy utilization.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Multidisciplinary Sciences
He Zhao, Yang Wu, Chenggang Ci, Zhenda Tan, Jian Yang, Huanfeng Jiang, Pierre H. Dixneuf, Min Zhang
Summary: The authors demonstrate a dearomative, diastereoselective annulation of azaarenes via ruthenium(II) reductive catalysis, showing excellent selectivity, mild conditions, and broad substrate and functional group compatibility, with the products formed via hydride transfer-initiated beta-aminomethylation and alpha-arylation of the pyridyl core.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Jiantao Fu, Zoe Vaughn, Andrew F. Nolting, Qi Gao, Dexi Yang, Christopher H. Schuster, Dipannita Kalyani
Summary: This manuscript presents the development of a diastereoselective intermolecular synthesis method for alkyl ethers using reductive etherification of various ketones or aldehydes with alcohols. The key aspect of this development is the utilization of low-temperature high-throughput experimentation (HTE) technologies for rapid reaction optimization and parallel synthesis. By carefully selecting the reductant, the diastereoselectivity of this transformation can be easily controlled.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Poorna Chandrasekhar Settipalli, Shaik Anwar
Summary: A [2+2+2] annulation reaction between cyclohexanone, beta-nitrostyrene and 2-arylidene-1,3-indanedione has been successfully carried out to obtain multisubstituted spiro trans-decalinol derivatives at room temperature. This reaction process exhibits high chemical yields and excellent diastereoselectivity, resulting in the formation of multiple bonds and stereocenters through the Michael/nitro-Michael/Aldol process.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Somi Kim, Junhyuk Jo, Sunggi Lee, Won-jin Chung
Summary: In this report, stereochemical modulation was achieved by utilizing pyridine-boryl radical to leave a synthetically modifiable boronate moiety during the cyclization step, leading to a successful catalytic synthesis of trans-2-substituted-1-indanols.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Yi Liu, Ji Li, Yulu Zhou, Hanliang Zheng, Zhenlu Shen, Gangguo Zhu
Summary: In this study, a visible-light-induced cascade radical cyclization method was developed for the synthesis of decorated a-fluoroalkyl cycloalkanols. The fluorine effect was found to play a crucial role in this reaction, as supported by density functional theory calculations.
CHINESE JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Chloe Herrle, Sami Fadlallah, Sylvestre Toumieux, Anne Wadouachi, Florent Allais
Summary: A novel method for synthesizing biobased diamide tetraol derivatives through mechanochemical processes is presented in this study. The use of planetary ball milling in the presence of a small excess of diamine was found to be crucial for achieving complete conversion of the key component and selective formation of the derivatives. The scalability of the process was demonstrated, and enzymatic polymerization of the derivatives was also explored.
Article
Chemistry, Organic
Xiyuan Zhang, Yanfeng Gao, Yitong Liu, Zhiwei Miao
Summary: The study reports a Diethyl phosphite-initiated reaction with [1,2]-phospha-Brook rearrangement, leading to the successful synthesis of a series of trans-tetrabenzohydrofuran spirooxindoles.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Ekaterina Levashova, Maria Adamchik, Grigory Kantin, Dmitry Dar'in
Summary: Here, a chemo- and diastereoselective formal C-C insertion reaction was described, which introduced 1,2-disubstituted 4-diazo-3(2H)-isoquinolones and 4-diazoisochroman-3-one into the C-CHO bonds of aldehydes, resulting in all-carbon α-quaternary aldehydes bearing medicinally important 1,4-dihydro-3(2H)-isoquinolone scaffold. The protocol exhibited preferential 1,2-carbon migration over the common 1,2-H shift, and the reaction tolerated various functionalities in both aldehyde and diazo components, providing the target homologated aldehydes in generally high yields. The synthetic utility of this method was further demonstrated by transformations of the formyl moiety.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Carlos Sedano, Cintia Virumbrales, Samuel Suarez-Pantiga, Roberto Sanz
Summary: The method proposed in this study can generate 1,2,3-triol fragments through a reaction, with excellent diastereoselectivity, and by overcoming some limitations of the previously reported method, broadens the application scope of polyols.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Multidisciplinary
Sandip B. Jadhav, Sundaram Maurya, N. Navaneetha, Rambabu Chegondi
Summary: In this study, highly diastereoselective arylative cyclization of enone-tethered cyclohexadienones via Rh(iii)-catalyzed C-H activation of N-methoxybenzamides was reported, providing access to functionalized bicyclic scaffolds with four contiguous stereocenters. The products exhibit excellent functional handles for further synthetic transformations to increase structural complexity. Mechanistic studies of arylative cyclization and a gram-scale experiment were also presented.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Akanksha Kumari, Anshul Jain, Khyati Shukla, Ranjan Patra, Nirmal K. Rana
Summary: We have developed a highly stereoselective formal [4 + 1] annulation reaction to construct trans-2,3-dihydrobenzofurans using in situ generated supported pyridinium ylide. This approach shows excellent substrate versatility and the capability of gram-scale synthesis. Moreover, the polymer-anchored pyridine can be recovered and reused multiple times. The product has been transformed into valuable molecules.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Pavel Yu. Ushakov, Sema L. Ioffe, Alexey Yu. Sukhorukov
Summary: In this work, the classical approach to aldol synthesis using isoxazoline was revisited. A [4 + 1] annulation reaction was used to construct the isoxazoline ring bearing an N-oxide moiety to avoid regioselectivity issues. The resulting alpha'-acyloxy-substituted aldols were obtained with good yields and as single diastereomers in most cases. The synthetic use of these aldols was demonstrated by their transformation into diastereomerically pure triols and a structurally related tetrahydrofuran derivative.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Aggie Lawer, Ryan G. Epton, Thomas C. Stephens, Kleopas Y. Palate, Mahendar Lodi, Emilie Marotte, Katie J. Lamb, Jade K. Sangha, Jason M. Lynam, William P. Unsworth
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Article
Chemistry, Physical
Aimee K. Clarke, Alison Parkin, Richard J. K. Taylor, William P. Unsworth, James A. Rossi-Ashton
Article
Chemistry, Physical
James A. Rossi-Ashton, Aimee K. Clarke, William P. Unsworth, Richard J. K. Taylor
Article
Chemistry, Organic
Nantachai Inprung, Michael J. James, Richard J. K. Taylor, William P. Unsworth
Summary: An operationally simple, high yielding three-step cascade process has been developed for the direct conversion of indole-tethered ynones into functionalized quinolines. A single multitasking thiol reagent is used to promote a three-step dearomatizing spirocyclization, nucleophilic substitution, and one-atom ring expansion reaction cascade under remarkably mild conditions. Additionally, a novel route to thio-oxindoles was discovered serendipitously.
Article
Chemistry, Organic
Nantachai Inprung, Hon Eong Ho, James A. Rossi-Ashton, Ryan G. Epton, Adrian C. Whitwood, Jason M. Lynam, Richard J. K. Taylor, Michael J. James, William P. Unsworth
Summary: Indole-ynones have been established as versatile substrates for radical dearomatizing spirocyclization cascade reactions, and five different synthetic protocols have been developed. These simple and readily available compounds can rapidly generate diverse, densely functionalized spirocycles and offer new avenues for exploring radical reactivity.
Article
Chemistry, Inorganic & Nuclear
Ryan G. Epton, William P. Unsworth, Jason M. Lynam
Summary: This study presents a convenient and mild method for the synthesis of vinyl indoles. High yields of 3-substituted indoles were obtained, and only one indole is added to the alkyne compared to reactions with simple alkynes. The method showed good tolerance towards different positions of indoles and ester-, amide-, and ketone-substituted alkynes.
Article
Biochemistry & Molecular Biology
Kleopas Y. Palate, Zhongzhen Yang, Adrian C. Whitwood, William P. Unsworth
Summary: A novel reaction sequence was reported for the preparation of medium-sized ring and macrocyclic bis-lactams through conjugate addition and ring expansion reactions. The reactions are simple, high yielding, and broad in scope, and can be performed iteratively for sequential ring expansion.
RSC CHEMICAL BIOLOGY
(2022)
Review
Chemistry, Multidisciplinary
Ryan G. Epton, William P. Unsworth, Jason M. Lynam
Summary: This review focuses on the application of density functional theory (DFT) in gold(I) catalysis, specifically discussing the importance of considering anions in calculations and the necessity of benchmarking computational results against experimental data for accurate modeling.
ISRAEL JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Zhongzhen Yang, Christopher R. B. Swanson, William P. Unsworth
Summary: This study presents a synthetic strategy based on consecutive ring-expansion reactions to synthesize analogues of the macrocyclic core of solomonamide natural products. By performing multiple ring-expansion reactions, amino acid and hydroxy acid derived fragments are inserted into the enlarged macrocyclic products.
Article
Chemistry, Multidisciplinary
Zhongzhen Yang, Illya Zalessky, Ryan G. Epton, Adrian C. Whitwood, Jason M. Lynam, William P. Unsworth
Summary: Two new strategies for synthesizing medium sized ring and macrocyclic sulfonamides are reported. These methods do not require classical protecting groups and involve nitro reduction and amine conjugate addition respectively for ring expansion. Both methods yield diversely functionalized cyclic sulfonamides in good to excellent yields, and the ring size dependency matches with Density Functional Theory calculations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Nantachai Inprung, Adrian C. Whitwood, Richard J. K. Taylor, Michael J. James, William P. Unsworth
Summary: This paper describes the dearomative spirocyclisation of benzisoxazoles through a radical chain mechanism. By utilizing stabilizing three-electron interactions, densely functionalized spirocycles can be obtained in high yields, which can be further converted into other spirocyclic scaffolds through a two-step hydrogenolysis-cyclisation sequence.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Environmental Sciences
Daniel J. J. Bryant, Alfred W. W. Mayhew, Kelly L. L. Pereira, Sri Hapsari Budisulistiorini, Connor Prior, William Unsworth, David O. O. Topping, Andrew R. R. Rickard, Jacqueline F. F. Hamilton
Summary: This study proposes a quantification method based on the prediction of relative ionisation efficiency factors to correct the concentrations of biogenic secondary organic aerosol species. The method was developed using commercially available standards and was able to predict the ionisation efficiency factors of biogenic organic acids without authentic standards. The concentration of biogenic secondary organic aerosol was corrected using the predicted factors and resulted in a significant decrease in average concentration.
ENVIRONMENTAL SCIENCE-ATMOSPHERES
(2023)
Article
Chemistry, Organic
Kleopas Y. Palate, Ryan G. Epton, Adrian C. Whitwood, Jason M. Lynam, William P. Unsworth
Summary: A side chain insertion method for the ring expansion of lactams into macrocyclic thiolactones is reported, which can also be incorporated into Successive Ring Expansion (SuRE) sequences. Despite being less thermodynamically favorable than analogous lactam- and lactone-forming ring expansion processes, three complementary protecting group strategies have been developed to enable this challenging transformation.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Review
Chemistry, Multidisciplinary
Aimee K. Clarke, William P. Unsworth
Article
Chemistry, Multidisciplinary
Hon Eong Ho, Angela Pagano, James A. Rossi-Ashton, James R. Donald, Ryan G. Epton, Jonathan C. Churchill, Michael J. James, Peter O'Brien, Richard J. K. Taylor, William P. Unsworth
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.
