Article
Chemistry, Organic
Kelvin J. Y. Wu, Amy E. Benedetto, Andrew G. Myers
Summary: The regioselectivity of a [3+2] dipolar cycloaddition reaction between a stabilized azomethine ylide and an electron-deficient dipolarophile is contrary to a previous report in this journal.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Sha Li, Yahan Sun, Xiaofang Li, Oskar Smaga, Sebastian Koniarz, Marcin Stepien, Piotr J. Chmielewski
Summary: A 1,3-cycloaddition reaction between 2-(tert-butyl)-8H-isoquinolino[4,3,2-de]phenanthridin-9-ium chloride and Ni-II norcorrole in the presence of base has been demonstrated to yield a family of chiral derivatives fused with pyrrole subunits of the macrocycle. Dehydrogenation of the cycloaddition products leads to dibenzoullazine ortho-fused antiaromatic porphyrinoids.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Asmaa Belabbes, Veronica Selva, Francisco Foubelo, M. De Gracia Retamosa, Jose M. Sansano
Summary: The synthesis of complex spiro{pyrrolidine-3,1'-pyrrolo[3,4-c]pyrrole} skeleton under mild conditions is presented, with the order of addition of a primary amine and two equivalents of corresponding maleimide being crucial for high yields. The mechanism was studied by simple tests, revealing the Michael type addition of the amine onto the maleimide as a key step. Interesting scaffold hybrids were prepared through sequential addition of two different maleimides, and a more intriguing architecture was obtained through a metathesis reaction between allylic residues in the molecule precursor.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Hooi Xian Lee, Wai Ming Li, Chee Wei Ang, Kerry Reimer, Victor Liu, Brian O. Patrick, Keng Yoon Yeong, Chow H. Lee
Summary: A facile three components (3 + 2) cycloaddition of two novel dispiropyrrolizidines was achieved, leading to unprecedented regioselectivity. The structures and activities of the synthesized compounds were determined through experimental techniques and structural analysis methods. The compounds exhibited the ability to down-regulate KRAS expression in human colorectal cancer cells.
JOURNAL OF MOLECULAR STRUCTURE
(2022)
Article
Chemistry, Multidisciplinary
Mohammed F. F. Radwan, Elghareeb E. E. Elboray, Hemat M. M. Dardeer, Yusuke Kobayashi, Takumi Furuta, Shohei Hamada, Toshifumi Dohi, Moustafa F. F. Aly
Summary: 1,3-Dipolar cycloaddition through in situ generation of azomethine ylide provides a straightforward and critically important sustainable approach for access to diverse pyrrolidine chemical space. Metal-free AcOH-activated 1,3-dipolar cycloaddition protocol was developed to synthesize uncommon pyrrolidine cycloadducts with excellent diastereoselectivity. The reaction mechanism and the key role of AcOH were supported by experimental, theoretical and spectroscopic studies.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
Article
Chemistry, Organic
Nagender Thadem, Manda Rajesh, Harikrishna Balaboina, Saibal Das
Summary: The synthesis of various bridged azacyclic adducts is an important topic due to their bioactive and natural product mimic profiles. In this study, a method for the easy access to succinamide-bridged azacyclic derivatives through a metal-free polarization-controlled dual C-N/C-C annulation is reported.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Sundaravel Vivek Kumar, Patrick J. Guiry
Summary: Asymmetric [3+2] cycloaddition reactions are interesting methods for synthesizing enantioenriched pyrrolidines with up to four stereocentres. Pyrrolidines are important compounds in biology and organocatalytic applications. This review summarizes the recent advancements in the enantioselective synthesis of pyrrolidines using metal catalysis, focusing on the [3+2] cycloadditions of azomethine ylides. The reactions are organized based on the type of metal catalysis and the complexity of the dipolarophile, highlighting their advantages and limitations.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Mariana Varde, Carla Marino, Evangelina Repetto, Oscar Varela
Summary: This study investigates the 1,3-dipolar cycloadditions starting from azomethine ylides and enantiomerically pure sugar-derived dihydropyranones. The reaction shows high regio- and diastereoselectivity under silver catalysis, resulting in the formation of pyrrolidine compounds with specific configurations.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Shohei Furuya, Kazuya Kanemoto, Shin-ichi Fukuzawa
Summary: This study describes an unprecedented Ag-catalyzed exo'-selective [3+2] cycloaddition reaction between imino esters and 4-benzylidene-2,3-dioxopyrrolidines. The reaction, efficiently catalyzed by Ag/(R, S-p)-ThioClickFerrophos (TCF), allows for the construction of spirobipyrrolidine scaffolds with excellent enantio- and diastereoselectivities. It is the first example of a silver-catalyzed exo'-selective asymmetric [3+2] cycloaddition and the first exo'-selective spirobipyrrolidine construction process using imino esters. The broad substrate scope of this reaction enables the synthesis of diverse spirobipyrrolidine derivatives, which are of interest for drug discovery. Mechanistic studies suggest that the unusual exo'-selectivity of this reaction is due to a stepwise Michael addition/Mannich sequence with bond rotation, rather than epimerization following the common exo- or endo-selective cycloaddition.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Article
Chemistry, Organic
Mamta Gill, Arko Das, Vinod K. Singh
Summary: An enantioselective (3+2) cycloaddition reaction has been reported for the synthesis of chiral polysubstituted pyrrolidines. The reaction displays opposite regioselectivity with excellent enantioselectivities and yields. Interestingly, changing the alpha-substituents of the iminoesters results in the formation of normal (3+2) cycloaddition products with excellent enantioselectivities as well.
Review
Biochemistry & Molecular Biology
Fatemeh Rostami Miankooshki, Mohammad Bayat, Shima Nasri, Narges Habibi Samet
Summary: This paper highlights the recent developments in the synthesis of spirooxindoles, focusing on representative synthetic methods and relevant reaction mechanisms from 2018 to 2021. It categorizes the synthetic methodologies based on the formation of azomethine ylide species from different starting materials.
MOLECULAR DIVERSITY
(2023)
Article
Chemistry, Organic
Jose Cortes Vazquez, Jacqkis Davis, Vladimir N. Nesterov, Hong Wang, Weiwei Luo
Summary: A formal [3 + 3] cyclization reaction has been developed for the synthesis of 1,3,4-oxadiazinanes with generally high yields (up to 96%). The reaction, catalyzed by Sc(OTf)(3), has a broad substrate scope for both diaziridines and quinones. The synergistic activation of 1,3-dipolar diaziridines and dipolar quinones was found to be essential for enabling this reaction.
Article
Biochemistry & Molecular Biology
Mezna Saleh Altowyan, Saied M. Soliman, Matti Haukka, Nora Hamad Al-Shaalan, Aminah A. Alkharboush, Assem Barakat
Summary: In this study, a novel heterocyclic hybrid of a spirooxindole system was synthesized by attaching ferrocene and triazole motifs into an azomethine ylide through a [3 + 2] cycloaddition reaction. The X-ray structure analysis revealed the expected structure of the heterocyclic hybrid and its crystallization in the triclinic-crystal system. Hirshfeld analysis provided insights into the molecular packing and identified the dominant intermolecular contacts in the crystal structure. AIM study indicated covalent characteristics for the Fe-C interactions.
Article
Chemistry, Organic
Xiaofeng Zhang, Xiaoming Ma, Wei Zhang
Summary: This article highlights recent work on the development of alpha-amino acid-based [3 + 2] cycloaddition reactions of N-H-type AMYs in multicomponent, one-pot, and stepwise reactions for the synthesis of diverse heterocycles related to some bioactive compounds and natural products.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Diksha Bhardwaj, Ruby Singh
Summary: A series of new functionalized analogues of spirooxindole-pyrrolidines have been synthesized via 1,3-dipolar cycloaddition reaction strategy under efficient and eco-friendly conditions. The reaction formed a complex heterocyclic hybrid with multiple stereo centers in one step, showcasing a high regio- and exo-selective manner. Single crystal X-ray diffraction analysis was used to determine the regio-/stereochemistry.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Organic
Daniel W. Klosowski, J. Caleb Hethcox, Daniel H. Paull, Chao Fang, James R. Donald, Christopher R. Shugrue, Andrew D. Pansick, Stephen F. Martin
JOURNAL OF ORGANIC CHEMISTRY
(2018)
Review
Chemistry, Multidisciplinary
Daniel H. Paull, Ciby J. Abraham, Michael T. Scerba, Ethan Alden-Danforth, Thomas Lectka
ACCOUNTS OF CHEMICAL RESEARCH
(2008)
Article
Chemistry, Multidisciplinary
Chao Fang, Charles S. Shanahan, Daniel H. Paull, Stephen F. Martin
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2012)
Article
Chemistry, Multidisciplinary
Ciby J. Abraham, Daniel H. Paull, Tefsit Bekele, Michael T. Scerba, Travis Dudding, Thomas Lectka
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2008)
Article
Chemistry, Multidisciplinary
Daniel H. Paull, Michael T. Scerba, Ethan Alden-Danforth, Leland R. Widger, Thomas Lectka
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2008)
Article
Chemistry, Multidisciplinary
Jeremy Erb, Daniel H. Paull, Travis Dudding, Lee Belding, Thomas Lectka
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2011)
Article
Chemistry, Multidisciplinary
Daniel H. Paull, Chao Fang, James R. Donald, Andrew D. Pansick, Stephen F. Martin
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2012)
Article
Chemistry, Organic
Chao Fang, Daniel H. Paull, J. Caleb Hethcox, Christopher R. Shugrue, Stephen F. Martin
Review
Chemistry, Organic
Daniel H. Paull, Anthony Weatherwax, Thomas Lectka
Article
Chemistry, Multidisciplinary
Elizabeth A. Recker, Matthew Green, Mohammad Soltani, Daniel H. Paull, Gregory J. McManus, James H. Davis, Arsalan Mirjafari
Summary: This study presents a novel approach using ionic liquids (ILs) for direct carbon capture from the atmosphere. The liquid salts based on a mixture of amino acids showed good sorption and sequestration efficiency for low concentration CO2. ILs derived from waste amino acids have potential in CO2 transformation and waste utilization.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2022)
Article
Chemistry, Multidisciplinary
Elizabeth A. Recker, Matthew Green, Mohammad Soltani, Daniel H. Paull, Gregory J. McManus, James H. Davis, Arsalan Mirjafari
Summary: Direct capture of CO2 from the atmosphere is a pressing task, and this article presents an innovative approach using ionic liquids (ILs) as sorbents. The results show that ILs derived from amino acids are effective in capturing CO2 with high efficiency and stability, making them a superior alternative to current methods.
ACS SUSTAINABLE CHEMISTRY & ENGINEERING
(2022)
Article
Chemistry, Organic
Daniel H. Paull, Ethan Alden-Danforth, Jamison Wolfer, Cajetan Dogo-Isonagie, Ciby J. Abraham, Thomas Lectka
JOURNAL OF ORGANIC CHEMISTRY
(2007)
Article
Chemistry, Organic
Cajetan Dogo-Isonagie, Tefsit Bekele, Stefan France, Jamison Wolfer, Anthony Weatherwax, Andrew E. Taggi, Daniel H. Paull, Travis Dudding, Thomas Lectka
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2007)
Article
Chemistry, Multidisciplinary
Daniel Paull, Jamison Wolfer, James W. Grebinski, Anthony Weatherwax, Thomas Lectka
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.