Article
Chemistry, Organic
Lisi Yuan, Ya Fang, Zhaobo Zhou, Tinghong Lv, Yingpeng Su, Jian Liu, Xiaolei Wang
Summary: This Letter describes a highly diastereoselective synthesis method for C-hydroxymethine glycosides from glycal anomers using an achiral N-heterocyclic carbene-copper catalyst. The diastereoselectivity is controlled by both the stereocenter of the substrate and the chirality of the N-heterocyclic carbene-copper complex, independent of the stereochemistry of C5 and the anomeric position. This approach allows for the production of a diverse range of C-hydroxymethine glycosides using versatile glycals and various functionalized aldehydes.
Article
Chemistry, Organic
Anna Lo, David A. Gutierrez, Garrett Toth-Williams, James C. Fettinger, Jared T. Shaw
Summary: Lewis acid mediated allylations of beta-alkoxy N-tosyl imines using allyltrimethylsilane led to the formation of anti-selective 3-alkoxy homoallylic N-tosyl amines. Two methods of Cu(OTf)(2)-mediated allylations were reported, showing that diastereoselectivity can be achieved through the 1,3 acyclic stereocontrol of beta-chiral aldimines. The observed selectivity trends and computational evidence suggest that selectivity arises through the formation of a six-membered ring chelate.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Michael T. Pirnot, Edna Mao, Yu-hong Lam, John Limanto, Ryan D. Cohen, Cheol K. Chung, Eric M. Phillips
Summary: A new strategy for the synthesis of 2'-fluorinated nucleosides has been developed, involving electrophilic fluorination of a glycal to form a difunctionalized furanoside intermediate with high diastereoselectivity, followed by glycosylation with a variety of heteroaryl nucleophiles with good diastereoselectivities.
Article
Chemistry, Multidisciplinary
Ying Shao, Shijie Tian, Jie Zhu, Shengbiao Tang, Jiangtao Sun
Summary: We report a method for the synthesis of beta-lactams via a three-component reaction. The method is straightforward, has a broad substrate scope, and provides moderate to good yields with excellent diastereoselectivity.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Anastasiia Klochkova, Andrey Bubyrev, Dmitry Dar'in, Olga Bakulina, Mikhail Krasavin, Viktor Sokolov
Summary: A novel tandem approach has been developed for the synthesis of various isothiazolidine 1,1-dioxides. The method involves N-alkylation of methanesulfonanilides with EWG-substituted allyl bromides followed by intramolecular Michael addition, leading to high yields and trans-diastereoselectivity. The reactivity dependency on the electronic properties of substrates has been investigated.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Organic
Rajni Lodhi, Meher Prakash, Sampak Samanta
Summary: Interesting desymmetric [3 + 2] annulation reactions between p-quinamines and 2-aroyl-1-chlorocyclopropanecarboxylates facilitated by a base lead to the formation of a unique class of cyclopropane-fused hydoindol-5-one frameworks with multiple stereogenic centers, showing promising diastereoselectivities. Importantly, a polycyclic tacrine analogue for treating Alzheimer's disease was synthesized using this developed method.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Zhaohui Cui, Kuan Zhang, Lijie Gu, Zhanwei Bu, Junwei Zhao, Qilin Wang
Summary: A highly diastereoselective dearomative trifunctionalization method has been established for pyridinium salts, using multifunctional o-hydroxyl aromatic azomethine ylides. This method allows for convenient and rapid assembly of challenging and architecturally crowded compounds, and represents a successful example of higher-order multifunctionalization of pyridiniums.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Physical
Helya J. Ghazvini, Hormoz Khosravi, Saber Mirzaei, Saeed Balalaie, Bernhard Breit
Summary: An innovative method for the selective formation of Z-vinyl-functionalized oxazoles via a rhodium-catalyzed nucleophilic addition of alpha-acidic isocyanoacetamides to allenes is described. By employing diverse isocyanoacetamides and allenes, a library of vinyl oxazoles can be efficiently synthesized in a stereo- and regiospecific manner. Mechanistic investigations reveal that the reaction proceeds through a concise rhodium-catalyzed ene reaction followed by reductive elimination.
Article
Chemistry, Multidisciplinary
Yuanjun Sun, Wenhao Tang, Huxin Ni, Mei Wang, Bin Huang, Ya-Qiu Long
Summary: The concise synthesis of the tetrahydropyranyl side chain of verucopeptin, an antitumor antibiotic cyclodepsipeptide, allows for structural modification and mechanism study, providing potential clinical applications.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Applied
Kanokwan Jaithum, Jumreang Tummatorn, Bundet Boekfa, Charnsak Thongsornkleeb, Kittipong Chainok, Somsak Ruchirawat
Summary: A method using a silver catalyst and acid for the diastereoselective synthesis of spirocyclic ethers has been developed, showing good yields of 97% and broad substrate applicability. The proposed reaction mechanisms and stereoselectivity outcomes have been investigated using DFT calculation.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Physical
Amaan M. Kazerouni, Daniel S. Brandes, Cassondra C. Davies, Laura F. Cotter, James M. Mayer, Shuming Chen, Jonathan A. Ellman
Summary: In this study, a photoredox-mediated hydrogen atom transfer approach was developed for the epimerization of delta-lactams to access the more stable anti diastereomers. The method exhibited broad functional group compatibility and the observed diastereoselectivities were consistent with the calculated relative stabilities. Deuterium labeling and luminescence quenching studies provided further insights into the reaction mechanism.
Article
Chemistry, Organic
Tongxu Xiang, Yongze Liu, Qiaoling Xu, Kehan He, Fei Pan
Summary: In this study, we developed a novel synthetic method for regio- and diastereoselective difluoromethylthiolation of acrylamides using palladium catalysis. The reaction exhibited high efficiency and showed good functional group tolerances under mild conditions, allowing access to compounds with SCF2H-containing skeletons. Mechanistic studies and post-functionalization of the product reactions were also conducted to provide insights into the reaction mechanism.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Amjad Ali, Raveena Jajoria, Harish K. Harit, Ravi P. Singh
Summary: In this study, the addition of alpha-ketoamide top-quinone methide initiated by dialkylphosphite in the presence of organic base DBU was explored. The coupling of dialkylphosphites to alpha-ketoamides followed[1,2]-phospha-Brook rearrangement, generating alpha-phosphonyloxy enolates that were subsequently seized by p-quinonemethides. This two-step one-pot 1,6-conjugate addition method provides effective access to a series of isatin-incorporated phosphate-bearing 1,6-adducts with high yield and selectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Shinichiro Fuse, Sena Kanda, Hisashi Masui
Summary: Valuable indole derivatives were synthesized via the sequential 1,2-addition/nucleophilic substitution of indolyl-3-carbaldehydes. Microflow technology was used to suppress undesired reactions caused by unstable intermediates, leading to higher yields and reproducibility. The study provides a rapid and efficient method for the synthesis of structurally diverse indole derivatives.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Florian Bourriquen, Julien Hervochon, Ruiyang Qu, Stephan Bartling, Nils Rockstroh, Kathrin Junge, Cedric Fischmeister, Matthias Beller
Summary: A convenient and practical diastereoselective cis-hydrogenation method for multi-substituted pyridines and arenes was reported. The use of a novel heterogeneous ruthenium catalyst resulted in high yields (typically >80%) of corresponding piperidines and cyclohexanes with good functional group tolerance under mild conditions. The robust ruthenium supported catalyst can be easily prepared and reused multiple times without loss of activity.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Yogesh Jaiswal, Yogesh Kumar, Jagannath Pal, Ranga Subramanian, Amit Kumar
CHEMICAL COMMUNICATIONS
(2018)
Article
Chemistry, Organic
Yogesh Kumar, Yogesh Jaiswal, Amit Kumar
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Organic
Yogesh Jaiswal, Yogesh Kumar, Amit Kumar
JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Multidisciplinary
Yogesh Kumar, Yogesh Jaiswal, Rima Thakur, Amit Kumar
Article
Chemistry, Organic
Ismail Althagafi, Ranjay Shaw, Cheng-Run Tang, Rahul Panwar, Shally, Chanda Sinha, Amit Kumar, Yong-Tang Zheng, Ramendra Pratap
ORGANIC & BIOMOLECULAR CHEMISTRY
(2018)
Article
Chemistry, Organic
Yogesh Kumar, Yogesh Jaiswal, Amit Kumar
Article
Chemistry, Organic
Mukta Shaw, Rima Thakur, Amit Kumar
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Mukta Shaw, Amit Kumar
Article
Chemistry, Multidisciplinary
Mukta Shaw, Amit Kumar
CHEMISTRY-AN ASIAN JOURNAL
(2019)
Article
Chemistry, Physical
Yogesh Jaiswal, Amit Kumar
CATALYSIS COMMUNICATIONS
(2019)
Article
Chemistry, Organic
Yogesh Jaiswal, Saptarshi Mandal, Prolay Das, Amit Kumar
Article
Chemistry, Organic
Akanksha Singh Baghel, Yogesh Jaiswal, Amit Kumar
Review
Chemistry, Organic
Rima Thakur, Yogesh Jaiswal, Amit Kumar
ORGANIC & BIOMOLECULAR CHEMISTRY
(2019)
Article
Chemistry, Organic
Yogesh Jaiswal, Yogesh Kumar, Amit Kumar
ORGANIC & BIOMOLECULAR CHEMISTRY
(2019)
Article
Chemistry, Organic
Mukta Shaw, Amit Kumar, Rima Thakur
TRENDS IN CARBOHYDRATE RESEARCH
(2017)
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.
