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.
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
Chemistry, Organic
Linlong Dai, Qiaohong Zhu, Jie Zeng, Yuheng Liu, Guofu Zhong, Xiaoyu Han, Xiaofei Zeng
Summary: The study presents an effective strategy for the synthesis of chiral imidazolidines through catalytic reactions, achieving high yields and enantioselectivities. Additionally, this method can also be applied in the synthesis of chiral vicinal diamines by adjusting the reaction conditions.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Ruo-Qing Wang, Chong Shen, Xiang Cheng, Xiu-Qin Dong, Chun-Jiang Wang
Summary: In this study, copper-catalyzed asymmetric propargylic substitution was successfully achieved using salicylaldehyde-derived imine esters and propargylic carbonates, resulting in a wide range of chiral amino acid derivatives containing propargylic groups. The ortho-hydroxy group of the salicylaldehyde-derived imine esters played a crucial role in increasing reactivity and stabilizing the azomethine ylide.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Xiaofeng Zhang, Weiqi Qiu, Stephanie A. Murray, Desheng Zhan, Jason Evans, Jerry P. Jasinski, Xiao Wang, Wei Zhang
Summary: A pseudo-five-component reaction is developed for the diastereoselective synthesis of unique butterfly shaped compounds with a plane of symmetry, involving double decarboxylative 1,3-dipolar cycloaddition of azomethine ylides with olefinic oxindoles. The reaction is promoted by recyclable zeolite HY acid catalyst, and only CO2 and H2O are generated as byproducts.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Tobias Sandmeier, Erick M. Carreira
Summary: The study introduces the enantio- and chemoselective N-allylation of oximes, yielding cyclic nitrones and enantioenriched aliphatic allylic alcohols through intramolecular kinetic resolution. The method stands out for its ability to utilize E/Z-isomeric oxime mixtures convergently and high functional group tolerance, showcasing its synthetic utility with the formal synthesis of (+)-halichlorine.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Biochemistry & Molecular Biology
Alexei N. Izmest'ev, Valentina A. Karnoukhova, Alexander A. Larin, Angelina N. Kravchenko, Leonid L. Fershtat, Galina A. Gazieva
Summary: This study proposes methods for the synthesis of two types of isomeric dispirocompounds based on imidazothiazolotriazine and pyrrolidineoxindole. The first method involves a 1,3-dipolar cycloaddition and column chromatography to obtain a mixture of isomers. The second method involves rearrangement to obtain the other isomer.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Biochemistry & Molecular Biology
Guipeng Feng, Guoyang Ma, Wenyan Chen, Shaohong Xu, Kaikai Wang, Shaoyan Wang
Summary: The [3 + 2] 1,3-dipolar cycloaddition of C,N-cyclic azomethine imines with allyl alkyl ketones has been achieved, resulting in a range of tetrahydroisoquinoline derivatives with good diastereoselectivities and enantioselectivities. The absolute configuration of the product was determined using quantum electronic circular dichroism calculation and ECD spectrum method.
Article
Chemistry, Multidisciplinary
Houda Gazzeh, Fadwa Rouatbi, Sami Chniti, Moheddine Askri, Michael Knorr, Carsten Strohmann, Christopher Golz, Al Mokhtar Lamsabhi
Summary: The mechanism of a three-component one-pot cycloaddition reaction was studied using both theoretical and experimental methods. The reactivity difference between the unsymmetrical exocyclic dienones was analyzed to explain the observed regio- and stereoselectivity, and the results were confirmed by calculations. The reaction proceeded under kinetic control and showed chemoselectivity, producing two highly diastereomerically enriched compounds. The intermolecular hydrogen bonding and optical properties of the products were also investigated.
NEW JOURNAL OF CHEMISTRY
(2022)
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
Biochemistry & Molecular Biology
Ursa Stanfel, Dejan Slapsak, Uros Groselj, Franc Pozgan, Bogdan Stefane, Jurij Svete
Summary: Silica gel-bound Cu(II)-enaminone complexes were prepared and showed promising catalytic activity in CuAIAC reactions, but suffered from poor reusability. Improved reusability was achieved by using a 4-aminobenzoic acid linker attached to the enaminone via an amide bond.
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, Multidisciplinary
Stefan Flesch, Peter Voehringer
Summary: The chemical reactivity of nitrile imines is widely used in organic synthesis, but our understanding of their electronic and molecular structures is incomplete, and the photoinduced generation mechanism is unknown.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Review
Chemistry, Multidisciplinary
Mahzad Dehghany, Jennifer M. Schomaker
Summary: Silver offers a cost-effective alternative for asymmetric transformations of alkenes and alkynes, driving selectivity through non-covalent interactions. The reactions enable direct enantioselective transformations of the alkene/alkyne pi bond and functionalization at adjacent C-H bonds.
CURRENT OPINION IN GREEN AND SUSTAINABLE CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Xiaofeng Zhang, Miao Liu, Desheng Zhan, Manpreet Kaur, Jerry P. Jasinski, Wei Zhang
Summary: A three-component reaction of nonstabilized azomethine ylides derived from alpha-C-H functionalization of tetrahydroisoquinoline has been developed for the regio- and diastereoselective synthesis of spirooxindole-pyrrolidines. This method provides a pot, atom and step economy (PASE) approach for preparing spiro-heterocyclic compounds with biological interest, using readily available cyclic amines, aryl aldehydes, and olefinic oxindoles.
NEW JOURNAL OF CHEMISTRY
(2022)
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.