Article
Chemistry, Organic
Prabhat K. Maharana, Tanumay Sarkar, Subhradeep Kar, Siddhartha K. Purkayastha, Ankur K. Guha, Tharmalingam Punniyamurthy
Summary: Stereospecific C-N and C-O bond formation of oxiranes with diaziridines has been achieved using a bimetallic catalyst at room temperature, resulting in the production of tetrahydro-[1,3,4]-oxadiazines. Optically active oxiranes can be coupled with high optical purities (>96% ee). The practical significance of this method lies in its stereoselectivity, tolerance for various functional groups, mechanistic studies using DFT, and potential application in natural product modification.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Anil Kumar Soda, Krishna Prasad Chinthapally, C. S. Phani Krishna, Sai Krishna Chilaka, Sridhar Madabhushi
Summary: Under Lewis acid catalysis, the one-pot domino reaction between ethyl (Z)-3-amino-3-phenylacrylates and 2-amino-N-alkyl/arylbenzamides was used to construct novel spiro [pyrrole-3,2'-quinazoline] carboxylate derivatives. This method combines substituted alkyl/aryl amides with spiro annulated 1H-pyrrole-2,3-diones to produce spiro pyrrole derivatives in good to excellent yields. The current procedure offers advantages such as shorter reaction times, a broad tolerance range for functional groups, and the synthesis of biologically important 2,3-dihydroquinazolin-4(1H)-ones that can participate in organic transformations.
Article
Chemistry, Organic
Junwei Wang, Lin Zhao, Caihong Li, Lei Zhao, Kun Zhao, Yang Hu, Lihong Hu
Summary: An efficient synthetic approach using iridium-catalyzed [4+3] cyclization has been developed successfully, providing valuable seven-membered heterocyclic frameworks with high yield (up to 97%) and diastereoselectivity (dr>20:1).
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Qiwen Pang, Jin Zhou, Yuling Wu, Wu-Jingyun Zhou, Wei-Fang Zuo, Gu Zhan, Bo Han
Summary: Developing efficient strategies for synthesizing novel diazocine compounds is valuable due to limited synthetic accessibility. This work describes the catalytic reaction between carbonyl ylides and in situ generated azoalkenes, resulting in the synthesis of oxo-bridged diazocines. The product could be obtained on a gram scale and converted into diversely substituted dihydroisobenzofurans.
Article
Chemistry, Multidisciplinary
Suo-Suo Qi, Xin Luo, Xiao-Ping Sun, Jing-Jing Zhai, Ming-Ming Chu, Jin Chen, Yi-Feng Wang, Dan-Qian Xu
Summary: A sequential asymmetric conjugate addition/cyclisation of α-bromohydroxamates with para-quinone methide derivatives has been developed, providing enantioenriched 1,4-benzoxazepines in high yields (up to 95%) and good enantioselectivities (up to 97:3 er). This method offers a novel and straightforward strategy for constructing chiral 1,4-benzoxazepines, and demonstrates the potential of α-bromohydroxamates as three-atom synthons in asymmetric cyclisation reactions.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Jakub Brzes, Rafal Loska
Summary: A palladium-catalyzed strategy for constructing isoindole N-oxide ring by C-H functionalization of aldonitrones is presented. The protocol is versatile and allows for the introduction of various functional groups, even in sterically congested products. Transformations into spirocyclic isoindolines, isoindoles, and polycyclic isoquinolinium salt have also been demonstrated. Mechanistic studies suggest a Heck-type addition to the double C=N bond as the catalytic process.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Jakub Brzeskiewicz, Rafal Loska
Summary: The palladium-catalyzed C(sp(2))-H functionalization of bromoaryl aldonitrones leading to benzocyclobutenone-derived ketonitrones is described. This method allows for the preparation of a wide range of strained, four-membered ketonitrones with broad functional group tolerance. Downstream transformations of the formed products were readily demonstrated, illustrating the synthetic utility of the obtained benzocyclobutenone-derived nitrones for the construction of polycyclic nitrogen-containing scaffolds.
Article
Chemistry, Applied
Yan Wang, Li-Ming Zhao
Summary: We have disclosed a simple and general method for the synthesis of chromendiones through Rh(III)-catalyzed C-H functionalization/annulation reactions of nitrones with cyclic 2-diazo-1,3-diones by using nitrones as a traceless directing group. This method shows high efficiency and wide functional group compatibility. The derivatization of these chromendiones has also been demonstrated to enhance the synthetic utility of the transformation.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Maniyamma Aswathy, Mohammed N. K. Sadik, Purushothaman C. Harikrishnan, Sasikumar Parameswaran, Kokkuvayil Vasu Radhakrishnan, Ravi S. Lankalapalli
Summary: This paper describes a method for stereoselective glycosylation using a chiral Bronsted acid, the (+)-isomenthol ester of pentacarbomethoxycyclopentadiene, with n-pentenyl glycosides in the presence of N-iodosuccinimide as the promoter, which offers a chiral recognition of racemic substrates.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Yao Xu, Hai-Xiang Gao, Chengkai Pan, Yue Shi, Chi Zhang, Genping Huang, Chao Feng
Summary: By using photoredox catalysis, we have achieved the (3+3) dipolar cycloaddition of nitrones with aryl cyclopropanes. This reaction exhibits excellent regio- and stereoselectivity and can be applied to a variety of aryl cyclopropane substrates.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Junghyea Moon, Nayoung Ko, Seoeun Jang, Prithwish Ghosh, Hyung Sik Kim, Neeraj Kumar Mishra, In Su Kim
Summary: This paper describes the ruthenium(II)-catalyzed tandem C-H allylation and intramolecular dipolar cycloaddition reaction, which can form bridged tetracycles bearing a hydroxymethylene group at a bridgehead carbon center. The reaction exhibits a wide substrate scope and broad functional group compatibility.
Article
Chemistry, Organic
Michael P. Doyle, Ming Bao
Summary: This study achieved a highly enantioselective synthesis of substituted pyrrolidines and 1,2-oxazinanes via stereoretentive [3 + 2]/[3 + 3]-cycloaddition of nonracemic donor-acceptor cyclopropanes with imines, triazines, and nitrones. The reactions were conducted under mild conditions and showed good to high yields with broad applicability. Compared to previous approaches using racemic cyclopropane reactants and chiral ligand catalysts, this study utilized enantioenriched donor-acceptor cyclopropanes as reactants with achiral catalysts.
Article
Chemistry, Organic
Luis R. Domingo, Mar Rios-Gutierrez, Nivedita Acharjee
Summary: The BF3 Lewis acid catalyzed [3+2] cycloaddition reaction was studied using molecular electron density theory, and it was found that BF3 acts as a catalyst, increasing the polarity of the reaction and decreasing the activation enthalpy.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Pawan S. Dhote, Chepuri Ramana
Summary: The [Au]-catalyzed nitroalkyne cycloisomerization process leading to anthranils may be affected by the trapping of the postulated intermediate alpha-oxo gold carbene with external nucleophiles. This study also provides evidence for the synthesis of highly functionalized indazoles through sequential bond formations.
Article
Chemistry, Organic
Katarina Stefkova, Michael G. Guerzoni, Yara van Ingen, Emma Richards, Rebecca L. Melen
Summary: Here, a mild, transition-metal-free, highly diastereoselective Lewis acid catalyzed methodology for the synthesis of isoxazolidine-based diazo compounds from the reaction between vinyldiazo esters and nitrones is reported. Interestingly, the diastereoselectivity of the isoxazolidine products is found to be contrasting to previous metal-catalyzed reactions. Furthermore, the same catalyst can be used with enol diazo esters, leading to the formation of Mukaiyama-Mannich products. These diazo products can be further functionalized to generate benzo[b]azepine and pyrrolidinone derivatives.
Article
Chemistry, Multidisciplinary
Stalin R. Pathipati, Angela van der Werf, Lars Eriksson, Nicklas Selander
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2016)
Article
Chemistry, Organic
Hai-Bin Yang, Nicklas Selander
ORGANIC & BIOMOLECULAR CHEMISTRY
(2017)
Article
Chemistry, Organic
Angela van der Werf, Matic Hribersek, Nicklas Selander
Article
Chemistry, Organic
Stalin R. Pathipati, Angela van der Werf, Nicklas Selander
SYNTHESIS-STUTTGART
(2017)
Article
Chemistry, Physical
Hai-Bin Yang, Stalin R. Pathipati, Nicklas Selander
Article
Chemistry, Organic
Stalin R. Pathipati, Angela van der Werf, Nicklas Selander
Article
Chemistry, Organic
Zhiyao Zheng, Angela van der Werf, Marie Deliaval, Nicklas Selander
Article
Chemistry, Organic
Linpeng Liu, Yanyu Jian, Weigao Hu, Shaohu Zhao, Zhang-Jie Shi, Nicklas Selander, Taigang Zhou
Summary: A method for radical cyclization and ring-opening of oxime esters with diselenides has been developed. Both Ni(0) and Fe(ii) catalysts can be used for the selenylation of olefin-containing and cyclic oxime ester derivatives. Using this method, a variety of functionalized pyrrolines and alkyl nitriles can be synthesized in good yields. Additionally, a mechanism involving iminyl radical and carbon-centered radical intermediates has been proposed.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Stalin R. Pathipati, Lars Eriksson, Nicklas Selander
CHEMICAL COMMUNICATIONS
(2017)
Article
Chemistry, Multidisciplinary
Hai-Bin Yang, Nicklas Selander
CHEMISTRY-A EUROPEAN JOURNAL
(2017)