Article
Chemistry, Multidisciplinary
Changli He, Xiaoxue Tang, Xin He, Yuqiao Zhou, Xiaohua Liu, Xiaoming Feng
Summary: Reversal of regioselectivity in the catalytic asymmetric conjugate additions of 3-substituted oxindoles to beta-nitroenones or beta-nitroacrylates was achieved with chiral scandium catalysts. Functionalized 3,3-disubstituted oxindoles, including terminal and internal vinyl groups, were constructed in excellent yields and ee values.
CHINESE CHEMICAL LETTERS
(2023)
Article
Chemistry, Organic
Ehsan Sheikhi, Narjes Rezaei, Alvaro Castilla, Amparo Sanz-Marco, Carlos Vila, M. Carmen Munoz, Jose R. Pedro, Gonzalo Blay
Summary: An enantioselective organocatalytic addition of sodium bisulfite to (E)-nitroalkenes has been developed using a chiral bifunctional organocatalyst, providing a variety of chiral beta-nitroethanesulfonic acid compounds. The reaction demonstrates high yield and excellent enantioselectivity under the reaction conditions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Aabid A. Wani, Kriti Mehta, Rajeswara Reddy, Prasad V. Bharatam
Summary: This article reports the 1,1-diaminoazine-catalysed Michael addition reaction of malonates with nitro-olefins. The bifunctional nature of the catalyst facilitates the C-C bond formation.
NEW JOURNAL OF CHEMISTRY
(2023)
Review
Chemistry, Applied
Sushovan Paladhi, Jin Hyun Park, Barnali Jana, Han Yong Bae, Choong Eui Song
Summary: This review summarizes recent advances in the construction of all-carbon quaternary or hetero-carbon quaternary stereocenters via metal-catalyzed and organocatalyzed asymmetric conjugate addition to β,β-disubstituted nitroalkenes, focusing on the scope, applications, and mechanisms of these reactions.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Oleg I. Afanasyev, Fedor S. Kliuev, Alexey A. Tsygankov, Yulia V. Nelyubina, Evgenii Gutsul, Valentin V. Novikov, Denis Chusov
Summary: This study demonstrates that the simple in situ addition of fluoride to asymmetric organometallic catalysts can improve both their activity and enantioselectivity. The approach has been successfully applied to prepare several enantioenriched GABA analogues.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Zubeda Begum, Haruka Sannabe, Chigusa Seki, Yuko Okuyama, Eunsang Kwon, Koji Uwai, Michio Tokiwa, Suguru Tokiwa, Mitsuhiro Takeshita, Hiroto Nakano
Summary: Simple primary beta-amino alcohols act as efficient organocatalysts in the asymmetric Michael addition of beta-keto esters with nitroalkenes, producing highly pure chiral Michael adducts. The choice of catalyst and reaction temperature determines the enantiomeric outcome of the adducts.
Article
Chemistry, Multidisciplinary
Debojyoti Bag, Sanghapal D. Sawant
Summary: This article presents the Ag(i)-catalyzed highly diastereoselective construction of divergent spiroindolines. The method involves dearomatizing spirocyclization of indole-tethered ynones followed by C-nucleophile or hydride trapping, leading to the formation of two new C-C bonds and two contiguous stereocenters. The strategy demonstrates broad applicability with (hetero)arenes as C-nucleophiles and exhibits excellent diastereoselectivity.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Gurupada Hazra, Sayantan Kundu, Rambabu Dandela, Barla Thirupathi
Summary: A facile synthetic approach for 6H-pyrrolo[3,2,1-de]acridines has been developed by using a cascade N-nucleophilic addition-cyclic Michael addition process. The reaction was conducted under metal-free conditions using arynes and indoles substituted with Michael acceptors. Additionally, photophysical studies showed that the newly synthesized pyrroloacridine compounds exhibited good fluorescence emission properties.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Daiki Ishii, Shin-ichi Hirashima, Kosuke Nakashima, Hiroshi Akutsu, Takaaki Sakai, Yasuyuki Matsushima, Masahiro Kawada, Tsuyoshi Miura
Summary: A new organocatalyst efficiently promotes the asymmetric direct vinylogous conjugate additions of alpha-angelica lactones to benzoyl acrylonitrile derivatives, resulting in products with excellent enantioselectivities. The chiral gamma,gamma-disubstituted gamma-butenolides obtained can be readily transformed to valuable synthetic intermediates.
Article
Chemistry, Organic
Chao Liu, Luc Van Meervelt, Vsevolod A. Peshkov, Erik V. Van der Eycken
Summary: A novel gold-catalyzed hydroarylation/Michael addition process has been developed for the efficient construction of benzazepinoindole polycyclic scaffolds from readily accessible multifunctional Ugi adducts. The developed methodology exhibits a broad substrate scope, excellent functional-group tolerance, and high yields of the target benzazepinoindoles.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Daeil Bae, Jin Won Lee, Do Hyun Ryu
Summary: New bifunctional secondary amine organocatalysts derived from L-proline were synthesized and applied in enantioselective Michael reactions in water, yielding high product yields and stereoselectivity. Investigations on the effect of phenyl group at (R)-C6 in the catalyst were conducted, and the successful formal synthesis of a novel histamine H3 receptor agonist, Sch 50971, demonstrated the synthetic utility of this reaction.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Pei Qu, Scott A. Snyder
Summary: The newly added annotinolides in the Lycopodium family have complex structures, and we have successfully achieved the total synthesis of three members using key operations such as gold(I)-catalyzed Conia-ene reaction and other challenging transformations. Furthermore, efforts to adjust the oxidation states and rearrange ring systems of the natural products shed light on their potential biogenesis.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Organic
Huanhuan Zou, Jiahang Yan, Xiaocheng Zhang, Xiaohui Wu, Jiyou Huo, Yuanzhen Xu, Weiqing Xie
Summary: In this study, the asymmetric synthesis of (+)-vellosimine was achieved in 13 steps (longest linear sequences, LLS). The synthesis featured a sequential nucleophilic addition/cyclization process and highlighted the reductive cyclization of a ketone with an attached alpha,beta-unsaturated ester for constructing the strained quinuclidine moiety.
Article
Chemistry, Organic
Shane R. Cochrane, Michael A. Kerr
Summary: This article describes the study on the reaction of 4-alkynyl indoles with benzylidene malonate or donor-acceptor cyclopropane in the presence of a zinc halide. The reaction proceeds via a tandem addition/Conia-ene cyclization and provides fair to excellent yields of 3,4-hexannylated or 3,4-heptannulated products.
Article
Chemistry, Multidisciplinary
Won Jun Jang, Jeongkyu Woo, Jaesook Yun
Summary: The study reported a method to synthesize enantioenriched alkylboron compounds through conjugate addition, which are influenced by two contiguous carbon stereogenic centers, with high yield and enantioselectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Multidisciplinary
Dong-Xing Zhu, Hui Xia, Jian-Guo Liu, Lung Wa Chung, Ming-Hua Xu
Summary: This study introduces for the first time the asymmetric insertion of an arylvinylcarbenoid into the C-H bond catalyzed by a rhodium(I)-diene complex, providing various chiral compounds with excellent enantioselectivity. Systematic DFT calculations were used to elucidate the reaction mechanism and origin of the uncommon enantioselectivity.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Medicinal
Jian-Wei Zhang, Yuan Xiong, Feng Wang, Fu-Mao Zhang, Xiaodi Yang, Guo-Qiang Lin, Ping Tian, Guangbo Ge, Dingding Gao
Summary: In this study, 9,10-dihydrophenanthrene derivatives were discovered as non-peptidomimetic and non-covalent inhibitors of SARS-CoV-2 3CL(pro). Among the tested compounds, C1 and C2 showed the most potent inhibition activity. Further experiments revealed that these compounds dose-dependently inhibit SARS-CoV-2 3CL(pro) and exhibit good metabolic stability.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Fu-Mao Zhang, Liang Yuan, Xin-Wei Shi, Kai-Rui Feng, Xiaojing Lan, Cheng Huang, Guo-Qiang Lin, Ping Tian, Min Huang, Shuai Tang, Dingding Gao
Summary: In this study, a novel PHGDH inhibitor, compound C25, was identified with improved enzymatic inhibitory activity and potent inhibitory activity on the proliferation of cells overexpressing PHGDH. Enzyme kinetic assay confirmed that C25 inhibited PHGDH in a competitive manner with NAD(+). Molecular docking and mutagenesis experiments revealed the binding site and key interaction residues of C25 in the PHGDH catalytic site, providing structural diversity for the development of potent PHGDH inhibitors.
BIOORGANIC CHEMISTRY
(2022)
Review
Chemistry, Medicinal
Feng Wang, Xin-Yu Cao, Guo-Qiang Lin, Ping Tian, Dingding Gao
Summary: This review summarizes the recent advances in the development of STAT3 inhibitors, focusing on the structure-activity relationships of different structural scaffolds.
EXPERT OPINION ON THERAPEUTIC PATENTS
(2022)
Article
Chemistry, Organic
Qi Liao, Da-Yu Shi, Hao Xu, Gui-Shan Zhang, Cheng Huang, Ping Tian, Guo-Qiang Lin, Zhengtao Wang, Yu-Hui Wang
Summary: An efficient synthesis of the stilbenoid lusianthridin is described, wherein a Suzuki-Miyaura coupling and an intramolecular nucleophilic substitution are employed as key reactions to construct the 9,10-dihydrophenanthrene core. The synthesis is accomplished in seven steps with a 13.2% overall yield, and each step can be conducted on a >20 gram scale. This route has provided 20 grams of lusianthridin for further biological activity studies.
Article
Chemistry, Multidisciplinary
Tian-Yi Wang, Xiao-Xuan Chen, Dong-Xing Zhu, Lung Wa Chung, Ming-Hua Xu
Summary: A highly selective C(sp(2))-H functionalization reaction catalyzed by rhodium(I)-diene has been developed, enabling the synthesis of α,β-unsaturated esters containing heteroatoms under mild reaction conditions. Mechanistic studies show that the substrate affects the reaction rate and selectivity.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Editorial Material
Multidisciplinary Sciences
Weici Xu, Ming-Hua Xu
CHINESE SCIENCE BULLETIN-CHINESE
(2022)
Article
Chemistry, Applied
Jia-Ying Zhao, Qi Liao, Jian-Wei Zhang, Guo-Qiang Lin, Zhengtao Wang, Dingding Gao, Qing-Hua Li, Ping Tian
Summary: In this study, a metal-free cascade dihalogenation-cyclization reaction was reported for the convenient preparation of dibrominated cis-tetrahydrobenzofuran-5(4H)-ones and cis-dihydrobenzopyran-6(5H)-ones. These products bear 1,4-dibromobut-1-enyl subunit in trans-trans and trans-cis form. The anticancer activity against MDA-MB-468 cells was also observed for the corresponding products.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Medicinal
Dingding Gao, Shuai Tang, Yixin Cen, Liang Yuan, Xiaojing Lan, Qing-Hua Li, Guo-Qiang Lin, Min Huang, Ping Tian
Summary: PHGDH is an important enzyme in serine biosynthesis pathway, and its overexpression in malignant tumor cells makes it a potential target for cancer treatment. In this study, a series of novel PHGDH inhibitors were discovered using compound screening and structural optimization. The lead compound D8 showed strong enzymatic inhibitory activity, high binding affinity, and sensitivity to PHGDH gene amplification or overexpression. Further experiments revealed the binding site of D8 on PHGDH and its potential antitumor efficacy in a xenograft mouse model.
JOURNAL OF MEDICINAL CHEMISTRY
(2023)
Article
Chemistry, Organic
Ya-Jie Wang, Yi-Fan Wang, Wen-Yu Kang, Wen-Ya Lu, Yu-Hui Wang, Ping Tian
Summary: Here, a highly enantioselective homoenolate Michael addition/esterification sequence of cyclo-hexadienone-tethered enals via N-heterocyclic carbene (NHC) catalysis is reported, leading to the formation of enantiopure cis-hydrobenzofurans, cis-hydroindoles, and cis-hydroindenes. The introduction of a nitro group in the NHC catalyst greatly enhances the stereocontrol, while a bulky N-aryl substituent in the triazolium salt is beneficial for preventing further aldol condensation. The utility of this method is demonstrated through a gram-scale experiment and versatile downstream transformations.
Article
Multidisciplinary Sciences
Qing-Hua Li, Gui-Shan Zhang, Feng Wang, Yixin Cen, Xi-Liang Liu, Jian-Wei Zhang, Yu-Hui Wang, Albert W. M. Lee, Dingding Gao, Guo-Qiang Lin, Ping Tian
Summary: Researchers report an asymmetric rearrangement of cyclopropylcarbinyl cations using artificial organic catalysts, resulting in chiral homoallylic sulfide products with high yields and enantioselectivities (up to 99% enantiomeric excess). The reaction involves the dehydration of prochiral cyclopropylcarbinols catalyzed by a chiral SPINOL-derived N-triflyl phosphoramide catalyst, followed by trapping of the resulting cyclopropylcarbinyl cations by thione-containing nucleophiles. The synthetic utility of the process is demonstrated through subgram-scale experiments and downstream transformations.
Article
Chemistry, Organic
Tao Wang, Ji-Xun Guan, Yun-Xuan Tan, Ping Tian
Summary: This paper reports the first cobalt-catalyzed highly selective arylation carbocyclization reaction of 1,6-allenynes with arylboronic acids. The reaction demonstrates moderate to high yields, broad substrate scope, and good compatibility with functional groups.
Article
Multidisciplinary Sciences
Bo-Ran Wang, Yan-Bo Li, Qi Zhang, Dingding Gao, Ping Tian, Qinghua Li, Liang Yin
Summary: A copper(I)-catalyzed asymmetric 1,3-dipolar cycloaddition of azomethine ylides and 1,3-enynes is reported, providing chiral poly-substituted pyrrolidines with high selectivities. 4-aryl-1,3-enynes and 4-silyl-1,3-enynes are suitable dipolarophiles, while 4-alkyl-1,3-enynes are inert. The method is capable of constructing tetrasubstituted stereogenic carbon centers and chiral spiro pyrrolidines. DFT calculations suggest a concerted mechanism. Transformations starting from the pyrrolidine bearing a triethylsilylethynyl group and centered on the alkyne group are achieved.
NATURE COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Pei-Ying Peng, Gui-Shan Zhang, Mei-Ling Gong, Jian-Wei Zhang, Xi-Liang Liu, Dingding Gao, Guo-Qiang Lin, Qing-Hua Li, Ping Tian
Summary: An efficient strategy for the preparation of bicyclic boronates through metal-free heteroatom-directed alkenyl sp2-C-H borylation is reported. The synthetic approach exhibits good functional group compatibility, and various boronates with halides, aryls, acyclic and cyclic frameworks are obtained in high yields (43 examples, up to 95% yield). Downstream transformations of the bicyclic boronates are also pursued to afford natural products, drug scaffolds, and chiral hemiboronic acid catalysts.
COMMUNICATIONS CHEMISTRY
(2023)
Article
Chemistry, Organic
Yu-Tuo Sun, Xiaofeng Rao, Weici Xu, Ming-Hua Xu
Summary: In this study, the first rhodium(I)-catalyzed asymmetric carbene insertion approach for C-S bond formation was developed using a chiral diene as a ligand. This method allows the synthesis of a range of potentially valuable alpha-thioesters in high yields with moderate to good enantioselectivities under mild conditions.
ORGANIC CHEMISTRY FRONTIERS
(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.
